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[ CAS No. 1196473-37-6 ] {[proInfo.proName]}

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Chemical Structure| 1196473-37-6
Chemical Structure| 1196473-37-6
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Quality Control of [ 1196473-37-6 ]

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Product Details of [ 1196473-37-6 ]

CAS No. :1196473-37-6 MDL No. :MFCD22200367
Formula : C7H7BO3 Boiling Point : -
Linear Structure Formula :- InChI Key :VVRHWLMUVDGIJJ-UHFFFAOYSA-N
M.W : 149.94 Pubchem ID :52919291
Synonyms :

Calculated chemistry of [ 1196473-37-6 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.14
Num. rotatable bonds : 0
Num. H-bond acceptors : 3.0
Num. H-bond donors : 2.0
Molar Refractivity : 40.74
TPSA : 49.69 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.9 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 0.45
Log Po/w (WLOGP) : 0.76
Log Po/w (MLOGP) : -0.66
Log Po/w (SILICOS-IT) : -1.37
Consensus Log Po/w : -0.16

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.05
Solubility : 13.3 mg/ml ; 0.0885 mol/l
Class : Very soluble
Log S (Ali) : -1.06
Solubility : 13.0 mg/ml ; 0.0868 mol/l
Class : Very soluble
Log S (SILICOS-IT) : 0.77
Solubility : 873.0 mg/ml ; 5.82 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 4.03

Safety of [ 1196473-37-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1196473-37-6 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 1196473-37-6 ]

[ 1196473-37-6 ] Synthesis Path-Downstream   1~12

  • 1
  • [ 1196473-37-6 ]
  • [ 352-11-4 ]
  • [ 1222010-61-8 ]
YieldReaction ConditionsOperation in experiment
88.4% 6-Hydroxyl-l,3-dihydro-l-hydroxy-2,l-benzoxaborole (lmmol) was dissolved in DMF (1OmL) and cooled to 00C with ice bath. To this solution under nitrogen were added in sequence sodium hydride (160mg, 4mmol, 4.0eq) and 1- (chloromethyl)-4-fluorobenzene (0.485mL, 4mmol, 4.0eq). The reaction mixture was stirred for 2 hours then treated with IM HCl (10ml). After extraction with ethyl acetate, the organic layer was washed with water and saturated brine. After rotary evaporation, the residue was purified by column chromatography over silica gel to give the title compound (228.2mg, 88.4percent yield). 1H NMR (300 MHz, DMSO-d6): delta 9.13 (s, IH), 7.53-7.11 (m, 7H), 5.10 (s, 2H) and 4.91 (s, 2H) ppm. Mp 136-137°C.
  • 2
  • [ 1196473-37-6 ]
  • [ 3958-60-9 ]
  • [ 1222010-64-1 ]
YieldReaction ConditionsOperation in experiment
40% Compound 42 (200 mg, 1.33 mmol) was dissolved in DMF (9.0 mL) and cooled to 0 0C with ice bath. To this solution under nitrogen were added in sequence NaH (60percent in mineral oil, 133 mg, 3.33 mmol) and l-(bromomethyl)-2-nitrobenzene (432 mg, 2.00 mmol). The reaction mixture was stirred for 1 h then treated with 1.0 M HCl (10.0 mL). After extraction with ethyl acetate, the organic phase was washed with water and saturated brine. After rotary evaporation, the residue was purified by column chromatography over silica gel to give the title compound (153 mg, 40percent yield). 1H NMR (300 MHz, DMSO-d6): delta 9.17 (s, IH), 8.15 (d, J = 7.2 Hz, IH), 7.83- 7.76 (m, 2H), 7.66-7.59 (m, IH), 7.37-7.30 (m, 2H), 7.15 (dd, J = 8.1 2.4 Hz, IH), 5.48 (s, 2H) and 4.92 (s, 2H) ppm; Mp: 135-138 0C.
  • 3
  • [ 1196473-37-6 ]
  • [ 345-35-7 ]
  • [ 1222010-58-3 ]
YieldReaction ConditionsOperation in experiment
55.7% 6-Hydroxyl-l,3-dihydro-l-hydroxy-2,l-benzoxaborole (lmmol) was dissolved in DMF (1OmL) and cooled to 00C with ice bath. To this solution under nitrogen were added in sequence sodium hydride (160mg, 4mmol, 4.0eq) and 1- (chloromethyl)-2-fluorobenzene (0.485mL, 4mmol, 4.0eq). The reaction mixture was stirred for 2 hours then treated with IM HCl (10ml). After extraction with ethyl acetate, the organic layer was washed with water and brine. The residue after rotary evaporation was purified by column chromatography over silica gel to give the title compound (143.6mg, 55.7percent yield). 1H NMR (300 MHz, DMSO-d6): delta 9.13 (s, IH), 7.58-7.12 (m, 7H), 5.16(s, 2H) and 4.92 (s, 2H) ppm. Mp 129-131°C.
  • 4
  • [ 1196473-37-6 ]
  • [ 103-71-9 ]
  • [ 1222010-52-7 ]
YieldReaction ConditionsOperation in experiment
18% 6-Hydroxyl-l,3-dihydro-l-hydroxy-2,l-benzoxaborole (0.667mmol) was dissolved in DMF (1OmL) and cooled to 00C with ice bath. To this solution under nitrogen were added in sequence triethylamine (0.28ml, 2mmol, 3.0eq) and isocyanatobenzene (0.852mL, 6.67mmol, lO.Oeq). The reaction mixture was stirred for 2 days at room temperature then treated with IM HCl (10ml). After extraction with ethyl acetate, the organic layer was washed with water and brine. The residue after rotary evaporation was purified by column chromatography over silica gel to give the title compound (32mg, 18percent yield). 1H NMR (300 MHz, DMSO-d6): delta 10.23 (s, IH), 9.25 (s, IH), 7.53-7.02 (m, 8H) and 5.00 (s, 2H) ppm.
  • 5
  • [ 1196473-37-6 ]
  • [ 3173-53-3 ]
  • [ 1222010-55-0 ]
YieldReaction ConditionsOperation in experiment
13% 6-Hydroxyl-l,3-dihydro-l-hydroxy-2,l-benzoxaborole (0.667mmol) was dissolved in toluene (1OmL) and cooled to 00C with ice bath. To this solution under nitrogen were added in sequence triethylamine (0.28ml, 2mmol, 3.0eq) and isocyanatocyclohexane (0.852mL, 6.67mmol, lO.Oeq). The reaction mixture was stirred for 2 days at room temperature then treated with IM HCl (10ml). The white solid was filtrated then purified by column chromatography over silica gel and recrystallization to give the title compound (24mg, 13percent yield). 1H NMR (300 MHz, Acetone-de): delta 8.09 (s, IH), 7.42-7.37 (m, 2H), 7.19 (dd, J = 8.4 2.1 Hz, IH), 6.65 (m, IH), 5.00 (s, 2H), 3.46 (m, IH) and 1.98-1.15 (m, 10H) ppm. Mp 198-2000C.
  • 6
  • [ 1222010-47-0 ]
  • [ 1196473-37-6 ]
YieldReaction ConditionsOperation in experiment
98% With hydrogen;palladium 10% on activated carbon; In methanol; at 20℃; H178 (13mmol) was dissolved in MeOH (300mL). To this solution under nitrogen was added 10percent Pd/C (200mg). The reaction mixture was vacuumed and backfilled hydrogen for 3 times, then stirred overnight at room temperature. After filtration and rotary evaporation, the residue was purified by recrystallization to give H181 (1.98mg, 98percent yield). 1H NMR (300 MHz, DMSO-d6): delta 9.29 (s, 1H), 9.04 (s, 1H), 7.18 (d, J = 8.4 Hz, 2H), 6.87 (dd, J = 8.1 2.4 Hz, 1H) and 4.86 (s, 2H) ppm. Mp 133-135°C.
98% With hydrogen;palladium 10% on activated carbon; In methanol; at 20℃;Inert atmosphere; H134 (13mmol) was dissolved in MeOH (30OmL). To this solution under nitrogen was added 10percent Pd/C (200mg). The reaction mixture was vacuumed and backfilled hydrogen for 3 times, then stirred overnight at room temperature. After filtration and rotary evaporation, the residue was purified by recrystallization to give the title compound (1.98mg, 98percent yield). 1H NMR (300 MHz, DMSO-d6): delta 9.29 (s, IH), 9.04 (s, IH), 7.18 (d, J = 8.4 Hz, 2H), 6.87 (dd, J = 8.1 2.4 Hz, IH) and 4.86 (s, 2H) ppm.
With hydrogen; palladium(II) hydroxide; In ethyl acetate; at 60℃; under 2585.81 Torr;Inert atmosphere; To the solution of 6-(benzyloxy)benzo[c][l,2]oxaborol-l(3H)-ol (50 g, 208 mmol) in EtOAc (800 mL) under nitrogen is added Pd(OH)2 (5g). The reaction mixture is vacuumed and back-filled with hydrogen for three times, and then hydrogenated at 60°C and 50 psi overnight. After filtration and rotary evaporation, the residue is purified by recrystallization to give the desired compound.
  • 7
  • [ 1196473-37-6 ]
  • [ 49608-01-7 ]
  • [ 1196473-56-9 ]
YieldReaction ConditionsOperation in experiment
To a solution of <strong>[1196473-37-6]3H-benzo[c][1,2]oxaborole-1,6-diol</strong> (1.2 g, 8.0 mmol) in anhydrous dioxane (100 mL) was slowly added KHMDS (48 mL, 0.5 M solution in toluene, 24.0 mmol) at 0° C. After stirring for 15 min at room temperature, 6-chloro-nicotinic acid ethyl ester (2.97 g, 16.0 mmol) was added slowly to the reaction mixture at 0° C. The resulting mixture was stirred at 80° C. for 22 h. The reaction quenched by adding cold brine at 0° C. and the mixture was acidified to pH 3 using diluted hydrochloric acid. The resulting mixture was extract with EtOAc. The extract was washed with brine, dried and concentrated to dryness. The residue was purified by chromatography on silica gel (DCM/methanol=40:1) to give 0.521 g of material. This material was purified by prep-TLC (silica gel, THF/hexanes/AcOH=2:4:trace) to give 0.261 g of purer material which was purified again by chromatography on silica gel (DCM/methanol=40:1) to give 0.109 g of pure product as a pale-yellow solid. Mp 84-85° C. 1H NMR (400 MHz, DMSO-d6) delta 9.23 (s, 1H), 8.68 (d, J=2.34 Hz, 1H), 8.31 (dd, J=8.50, 2.34 Hz, 1H), 7.41-7.54 (m, 2H), 7.30 (dd, J=8.20, 2.34 Hz, 1H), 7.15 (d, J=8.50 Hz, 1H), 5.02 (s, 2H), 4.32 (q, J=7.03 Hz, 2H), 1.31 (t, J=7.03 Hz, 3H). MS (ESI) m/z=300 [M+H]+.
  • 8
  • [ 33252-28-7 ]
  • [ 1196473-37-6 ]
  • [ 1196473-57-0 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate; In N,N-dimethyl-formamide; at 20 - 85℃; To a solution of <strong>[1196473-37-6]3H-benzo[c][1,2]oxaborole-1,6-diol</strong> (0.47 g, 3.13 mmol) in anhydrous DMF (15 mL) were added K2CO3 (1.30 g, 9.4 mmol) and 6-chloro-nicotinonitrile (0.868 g, 6.27 mmol) at room temperature. After stirring for 18 h at 85° C., the reaction mixture was cooled to room temperature. The solid was filtered out and dissolved into water (20 mL) and acidified to pH 3 using diluted hydrochloric acid. The precipitate was collected and washed with water and dried to give 0.612 g of crude product which was purified by recrystallization from EtOAc/hexanes to give 0.361 g of pure product as a white solid. Mp 156-157° C. 1HNMR (400 MHz, DMSO-d6) delta 9.25 (s, 1H), 8.64 (d, J=2.05 Hz, 1H), 8.33 (dd, J=8.50, 2.34 Hz, 1H), 7.40-7.53 (m, 2H), 7.19-7.32 (m, 2H), 5.02 (s, 2H). MS (ESI) m/z=253 [M+H]+.
  • 9
  • [ 1196473-37-6 ]
  • [ 33252-29-8 ]
  • [ 1196473-54-7 ]
YieldReaction ConditionsOperation in experiment
With caesium carbonate; In N,N-dimethyl-formamide; at 20 - 70℃; To a solution of <strong>[1196473-37-6]3H-benzo[c][1,2]oxaborole-1,6-diol</strong> (2.0 g, 13.33 mmol) in anhydrous DMF (8 mL) were added Cs2CO3 (10.86 g, 33.33 mmol) and 6-chloro-pyridine-2-carbonitrile (1.71 g, 14.0 mmol) at room temperature. After stirring at 70° C. for 8 h, the reaction mixture was cooled to 0° C. diluted with water (20 mL) and acidified to pH 3 using diluted hydrochloric acid. The mixture was extracted with EtOAc. The extract was washed with brine and dried to give the crude product which was purified by chromatography on silica gel (DCM/MeOH=40:2) to give 2.20 g of product. 1HNMR (400 MHz, DMSO-d6) delta 9.23 (br. s., 1H), 8.08 (m, 1H), 7.78 (d, J=7.33 Hz, 1H), 7.35-7.56 (m, 3H), 7.29 (dd, J=8.20, 2.05 Hz, 1H), 5.01 (s, 2H). MS (ESI) m/z=251 [M-H]-.
  • 10
  • [ 1196473-37-6 ]
  • [ 33332-25-1 ]
  • [ 1196473-63-8 ]
YieldReaction ConditionsOperation in experiment
5% With caesium carbonate; In N,N-dimethyl-formamide; at 20 - 90℃; To a solution of <strong>[1196473-37-6]3H-benzo[c][1,2]oxaborole-1,6-diol</strong> (0.37 g, 2.47 mmol) in anhydrous DMF (8 mL) were added Cs2CO3 (2.01 g, 2.71 mmol) and 5-chloro-pyrazine-2-carboxylic acid methyl ester (0.468 g, 2.71 mmol) at room temperature. After stirring at 90° C. for 1.5 h, the reaction mixture was cooled to 0° C., diluted with water (10 mL) and acidified to pH 3 using diluted hydrochloric acid. The off-white precipitate was collected, washed with water and dried to give the crude product which was purified by chromatography on silica gel (DCM/MeOH=40:3) to give 0.470 g (66.5percent yield) of product. MS (ESI) m/z=287 [M+H]+.
With caesium carbonate; In N,N-dimethyl-formamide; at 90℃; for 1.5h; To a solution of 20 (0.37 g, 2.47 mmol) in anhydrous DMF (8 mL) were added Cs2CO3 (2.01 g, 2.71 mmol) and 5-chloro-pyrazine-2-carboxylic acid methyl ester (0.468 g, 2.71 mmol) at room temperature. After stirring at 90 °C for 1.5 h, the reaction mixture was cooled to 0 °C, diluted with water (10 mL) and acidified to pH 3 using diluted hydrochloric acid. The off-white precipitate was collected, washed with water and dried to give the crude product which was purified by chromatography on silica gel (DCM/MeOH = 40:3) to give 0.47 g (66.5percent) of 21.
  • 11
  • [ 1196473-37-6 ]
  • [ 170235-26-4 ]
  • [ 1196473-65-0 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate; In N,N-dimethyl-formamide; at 80℃; for 24h; To a solution of <strong>[1196473-37-6]3H-benzo[c][1,2]oxaborole-1,6-diol</strong> (0.5 g, 3.33 mmol) in anhydrous DMF (15 mL) was added potassium carbonate (1.38 g, 9.99 mmol) followed by the addition of 2-bromo-thiazole-4-carboxylic acid methyl ester (0.74 g, 3.33 mmol). The resulting mixture was heated at 80° C. for 24 h. The reaction mixture was cooled and extracted with EtOAc, washed with water, brine, dried over Na2SO4, filtered, and concentrated to give crude product which was purified by prep HPLC using CH3CN/H2O (0.1percent AcOH) as the eluent to yield 2-(1-hydroxy-1,3-dihydro-benzo[c][1,2]oxaborol-6-yloxy)-thiazole-4-carboxylic acid methyl ester (0.01 g) as a white solid after lyophilization. Mp 109.2-111.5° C. 1H NMR (400 MHz, DMSO-d6) delta 9.34 (s, 1H), 8.08 (s, 1H), 7.62 (d, J=1.6 Hz, 1H), 7.56 (d, J=8.4 Hz, 1H), 7.47 (dd, J=8.4, 2.6 Hz, 1H), 5.03 (s, 2H), 3.78 (s, 3H). MS (ESI) m/z=292 [M+H]+.
  • 12
  • [ 947163-26-0 ]
  • [ 1196473-37-6 ]
YieldReaction ConditionsOperation in experiment
99.6% With boron tribromide; In dichloromethane; at -10 - 20℃; To a solution of 19 (10.0 g, 61.0 mmol) in dichloromethane (400 mL) was slowly added BBr3 (134 mL, 1 M in DCM, 0.134 mol) at -10 to -5 °C. The mixture was stirred at 0 °C to room temperature for 3 h. The reaction mixture was poured into ice-water (300 mL). The resulting mixture was extract with EtOAc (600 mL). The extract was washed with brine, dried and concentrated to dryness to give 9.11 g (99.6percent) of 20 as off-white foam.
99.6% With boron tribromide; In dichloromethane; at -10 - 20℃; To a solution of 6-methoxy-3H-benzo[c][1,2]oxaborol-1-ol (10.0 g, 61.0 mmol) in dichloromethane (400 mL) was slowly added boron tribromide (134 mL, 1 M in DCM, 0.134 mol) at -10 to -5° C. The mixture was stirred at 0° C. to room temperature for 3 h. The reaction mixture was poured into ice-water (300 mL). The resulting mixture was extract with EtOAc (600 mL). The extract was washed with brine, dried and concentrated to dryness to give 9.11 g (99.6percent yield) of product as off-white foam. 1H NMR (400 MHz, DMSO-d6) delta 9.27 (br. s., 1H), 9.03 (br. s., 1H), 7.16 (d, J=8.20 Hz, 1H), 7.08 (d, J=2.34 Hz, 1H), 6.86 (dd, J=8.20, 2.34 Hz, 1H). MS (ESI) m/z=151 [M+H]+.
2 g With boron tribromide; In dichloromethane; at -30 - 20℃; for 3h; Step 3: Intermediate 5-16b (2.500 g, 15.25 mmol, 1.0 eq) was dissolved in dichloromethane (100 mL) and cooled to -30.A 1 mol/L solution of boron tribromide in dichloromethane (60 mL, 60 mmol, 3.9 eq) was slowly added dropwise, and after completion of dropwise addition, the mixture was slowly warmed to room temperature for 3 hours.After the reaction was completed, the reaction mixture was poured into ice water (200 mL), and the mixture was separated, and the phases were separated. The aqueous phase was extracted with dichloromethane.Saturated brine (50mL), dried over anhydrous sodium sulfate, filtered and the filtrate was concentrated to give intermediate 5-16 total 2.00g.
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