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[ CAS No. 88675-24-5 ] {[proInfo.proName]}

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Chemical Structure| 88675-24-5
Chemical Structure| 88675-24-5
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Product Details of [ 88675-24-5 ]

CAS No. :88675-24-5 MDL No. :MFCD07778394
Formula : C4H9NO Boiling Point : -
Linear Structure Formula :- InChI Key :MIPHRQMEIYLZFZ-UHFFFAOYSA-N
M.W : 87.12 Pubchem ID :3365553
Synonyms :

Calculated chemistry of [ 88675-24-5 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 6
Num. arom. heavy atoms : 0
Fraction Csp3 : 1.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 23.02
TPSA : 35.25 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.3 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.24
Log Po/w (XLOGP3) : -0.66
Log Po/w (WLOGP) : -0.27
Log Po/w (MLOGP) : -0.57
Log Po/w (SILICOS-IT) : 0.6
Consensus Log Po/w : 0.07

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : 0.04
Solubility : 94.6 mg/ml ; 1.09 mol/l
Class : Highly soluble
Log S (Ali) : 0.39
Solubility : 216.0 mg/ml ; 2.47 mol/l
Class : Highly soluble
Log S (SILICOS-IT) : -0.04
Solubility : 80.2 mg/ml ; 0.92 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.45

Safety of [ 88675-24-5 ]

Signal Word:Danger Class:3,8
Precautionary Statements:P280-P305+P351+P338 UN#:2924
Hazard Statements:H225-H302-H315-H318 Packing Group:Ⅲ
GHS Pictogram:

Application In Synthesis of [ 88675-24-5 ]

* 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 [ 88675-24-5 ]

[ 88675-24-5 ] Synthesis Path-Downstream   1~11

  • 1
  • [ 88675-24-5 ]
  • [ 959938-25-1 ]
  • C22H22N2O5S [ No CAS ]
  • 2
  • [ 100390-87-2 ]
  • [ 88675-24-5 ]
YieldReaction ConditionsOperation in experiment
With hydrogen;palladium 10% on activated carbon; In methanol; hydrogen chloride; water; at 20℃; under 760.051 Torr; for 18h; [0152] 2) The N-benzyloxycarbonyl-3-aminotetrahydrofuran thus prepared (3.4 gm, 15 mmol) was dissolved in methanol (50 ml) and concentrated hydrochloric acid. Pd-C (10percent, 300 mg) was added, and the mixture was hydrogenated at 1 atmosphere for 18 hours at room temperature. The mixture was filtered through a pad of celite, and the filtrate concentrated under reduced pressure. The residue was co-evaporated twice with a mixture of ethyl acetate and methanol, and then recrystallized from a mixture of ethyl acetate and methanol to give 1.9 g of 3-aminotetrahydrofuran as a yellow solid.[0153] If the starting 3-tetrahydrofuroic acid is chiral, then the product (3-aminotetrahydrofuran) is also chiral, i.e., the synthesis is stereospecific.
  • 3
  • [ 88675-24-5 ]
  • [ 2004-06-0 ]
  • [ 204512-89-0 ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In methanol; at 80℃; for 40h; [0154] 3. A mixture of 6-chloropurine riboside (0.5 gm, 1.74 mmol), <strong>[88675-24-5]3-aminotetrahydrofuran</strong> (0.325 gm, 2.6 mmol) and triethylamine (0.73 ml, 5.22 mmol) in methanol (10 ml) was heated to 80° C. for 40 hours. The mixture was cooled and concentrated under reduced pressure. The residue was chromatographed on a short column of silica gel, eluting with methylene chloride/methanol/propylamine (90/10/1). The fractions containing the product were combined and concentrated under reduced pressure. The residue was chromatographed on a chromatotron (2 mm plate, 92.5/7.5/1, methylene chloride/methanol/propylamine). The resulting white solid was recrystallized from methanol/ethyl acetate to give 0.27 gm of (4S,2R,3R,5R)-2-hydroxymethyl-5-[6-(tetrahydrofuran-3-ylamino)-purin-9-yl]-tetrahydrofuran-3,4-diol as white crystals (mp 128° C.-130° C.).
  • 4
  • [ 88675-24-5 ]
  • [ 102191-92-4 ]
  • [ 786684-36-4 ]
YieldReaction ConditionsOperation in experiment
48% With sodium acetate; sodium tris(acetoxy)borohydride; acetic acid; In tetrahydrofuran; methanol; at 20℃; for 4.05h; a) A solution of TETRAHYDROFURAN-3-AMINE (see W098/08855, 0.500 g, 4.04 mmol) and sodium acetate (0.331 g, 4.04 mmol) in a 1: 3 mixture of methanol and tetrahydrofuran (60 ml) was stirred at room temperature. To this was added (tert-butyl- dimethylsilanyloxy) acetaldehyde (2.112 g, 12.12 mmol) followed by glacial acetic acid (1.456 g, 24.24 mmol) and then sodium triacetoxyborohydride (2.568 g, 12. 12 mmol) was then added in 5 portions over 3 minutes (CAUTION: vigorous effervescence) and the resulting suspension was left to stir at room temperature for 4 hours. The mixture was evaporated under reduced pressure to leave a thick brown paste which was dissolved in dichloromethane (20 ml) and to this was added a solution of ammonia in methanol (7M solution, 25 ml). The mixture was stirred for 10 minutes and then evaporated under reduced pressure to leave an orange paste which was triturated with dichloromethane (50 ml) and filtered through Celite. The mixture was evaporated under reduced pressure to leave a brown gum which was dissolved in methyl tert-butyl ether (3 ML) and then purified by silica gel chromatography using methyl tert-butyl ether as eluent to give N-(2-{ [TERT- butyl (dimethyl) silyl] oxy} ethyl) tetrahydrofuran-3-amine (0.446 g, 48percent yield) as a brown oil: 1H-NMR (CDC13) : 3. 68 (8H, m), 2. 68 (2H, m), 2.04 (1H, m), 1.73 (1H, m), 0. 82 (9H, s), 0.00 (6H, s).
  • 5
  • [ 88675-24-5 ]
  • [ 1493-27-2 ]
  • [ 767305-19-1 ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; In butan-1-ol; at 180℃; for 0.333333h;Microwave irradiation; Step A. (+/-)-N-(2-Nitrophenyl)tetrahvdrofuran-3 -amineA solution of N, jV-diisopropylethylamine (3.20 mL, 18.4mmol), l-fluoro-2- nitrobenzene (0.484 mL, 4.59 mmol), and (+/-)-tetrahydrofuran-3 -amine (400 mg, 4.59 mmol) in rc-butanol (10 mL) was heated to 180 0C in a microwave reactor. After 20 min, the reaction was allowed to cool to ambient temperature and concentrated. Purification by silica gel chromatography, eluting with a gradient of hexane: EtOAc - 100:0 to 0:100, gave the title compound. MS: mlz = 209 (M + 1).
With N-ethyl-N,N-diisopropylamine; In butan-1-ol; at 180℃; for 0.333333h;microwave reactor; A solution of N, N-diisopropylethylamine (3.20 mL, 18.4mmol), l-fluoro-2-nitrobenzene (0.484 mL, 4.59 mmol), and (+)-tetrahydrofuran-3 -amine (400 nig, 4.59 mmol) in 7z-butanol (10 mL) was heated to 180 0C in a microwave reactor. After 20 min, the reaction was allowed to cool to ambient temperature and concentrated. Purification by silica gel chromatography, eluting with a gradient of hexane:EtOAc - 100:0 to 0:100, gave the title compound. MS: mlz = 209 (M + 1).
  • 6
  • [ 88675-24-5 ]
  • [ 2004-06-0 ]
  • 6-(3-aminotetrahydrofuranyl)purine Riboside [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In methanol; Preparation of 6-(<strong>[88675-24-5]3-aminotetrahydrofuran</strong>yl)purine Riboside A mixture of 6-chloropurine riboside (0.5 gm, 1.74 mmol), <strong>[88675-24-5]3-aminotetrahydrofuran</strong> (0.325 gm, 2.6 mmol) and triethylamine (0.73 ml, 5.22 mmol) in methanol (10 ml) was heated to 80° C. for 40 hours. The mixture was cooled, and concentrated. The residue was filtered through a short column of silica gel eluding with 90/10/1 (CH2 Cl2 /MeOH/PrNH2) the fractions containing the product were combined and concentrated. The residue was chromatorgraphed on the chromatotron (2 mm plate, 92.5/7.5/1, CH2 CL2 /MeOH/Pr NH2). The resulting white solid was recrystallized from MeOH/EtOAc to give 0.27 gm of white crystals (mp 128°-130° C.).
  • 7
  • [ 88675-24-5 ]
  • [ 79-03-8 ]
  • N-(tetrahydrofuran-3-yl)propionamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In dichloromethane; N-(Tetrahydrofuran-3-yl)propionamide A solution of 50 g of <strong>[88675-24-5]3-aminotetrahydrofuran</strong> in 200 ml of dichloromethane was mixed with 63.8 g (0.63 mol) of triethylamine. 58.4 g (0.63 mol) of propionyl chloride were added dropwise with ice-cooling. The mixture was stirred at room temperature for 2 days, resulting in a white precipitate. The solution was filtered and the filtrate was distilled. B.p. 145° C. (12 mm), yield 81 g. 1H NMR (270 MHz, in CDCl3): delta=1.14 (t, 3 H), 1.83 (m, 1H), 2.22 (q, 2H), 2.31 (m, 1H), 3.64 (dd, 1H), 3.72-3.98 (m, 3H), 4.50 (m, 1H), 6.57 (s, 1H).
  • 8
  • [ 88675-24-5 ]
  • [ 1196452-58-0 ]
  • [ 13939-06-5 ]
  • [ 1196452-36-4 ]
YieldReaction ConditionsOperation in experiment
30% trans-di(mu-acetato)bis[o-(di-o-tolylphosphino)benzyl]dipalladium(II); tri tert-butylphosphoniumtetrafluoroborate; In tetrahydrofuran; at 125℃; for 0.166667h; To N-[(7i?, 2S)- 1 - { [ 1 -(3-bromophenyl)- 1 eta-indazol-5-yl]oxy } - 1 -(6-methoxypyridin-3- yl)propan-2-yl]-2,2-difluoropropanamide (37 mg, 68mumol), <strong>[88675-24-5]3-aminotetrahydrofuran</strong> (18 mg, 204mumol), tri-t-butylphosphoniumtetrafluoroborat (8.8 mg, 31 mumol) and trans- bis(acetato)bis[o-(di-o-tolylphosphino)-benzyl]dipalladium(II) (10.3 mg, 14mumol) in 1.5 mL THF was added molybdaenhexacarbonyl (12.5 mg, 47 mumol). The microwave vessel was closed and radiated in a microwave reactor (CEM discover) at 150 W and 125°C for 10 minutes (5 minutes ramp time. Then the solvent was removed i.vac, and the product purified by preparative thin layer chromatography on silica gel (ethyl acetate 100percent) to <n="57"/>yield 11 mg (30percent) 3-(5-[(7i?,25)-2-[(2,2-difluoropropanoyl)amino]-l-(6- methoxypyridin-3 -yl)propyl]oxy } - 1 H-indazol- 1 -y l)-N-(tetrahydrofuran-3 -yl)benzamide . ES+MS: m/z 580 [MH+]1H-NMR (300 MHz, CDCl3); delta = 8.20 (d, IH), 8.08 (dd, IH), 8.02 (s, IH), 7.83 (m, IH), 5 7.71 (m, IH), 7.67 (d, IH), 7.60 (dd, IH), 7.58 (t, IH), 7.16 (dd, IH), 6.99 (d, IH), 6.76 (d, IH), 6.66 (br, IH), 6.43 (br, IH), 5.36 (d, IH), 4.75 (m, IH), 4.40 (dq, IH), 4.01 (m,lH), 3.92 (s, 3H), 3.91 (m, IH), 3.83 (m, 2H), 2.38 (m, IH), 1.95 (m, IH), 1.77 (t, 3H), 1.29 (d, 3H).
  • 9
  • [ 88675-24-5 ]
  • [ 943134-39-2 ]
  • C18H24N4O4 [ No CAS ]
  • 10
  • [ 88675-24-5 ]
  • [ 1240402-60-1 ]
  • [ 1240401-22-2 ]
YieldReaction ConditionsOperation in experiment
25% With 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine; In toluene; at 50℃;Inert atmosphere; Example 4 3-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-isoxazole-5-carboxylic acid (tetrahydro-furan-3-yl)-amide To a solution of 3-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-isoxazole-5-carboxylic acid methyl ester (298 mg, 0.95 mmol) and <strong>[88675-24-5]tetrahydrofuran-3-ylamine</strong> (99 mg, 1.14 mmol) in toluene (1.5 mL) was added 1,5,7-triazabicyclo[4.4.0]dec-5-ene (40 mg, 0.28 mmol) and the reaction stirred under argon overnight at 50° C. Then the mixture was evaporated and the residue purified by chromatography (silica, heptane:ethyl acetate=4:1 to 1:1) to afford the title compound (87 mg, 25percent) which was obtained as a colourless gum. MS: m/e=370.1 [M+H]+.
  • 11
  • [ 88675-24-5 ]
  • [ 1246924-87-7 ]
  • [ 1246924-46-8 ]
YieldReaction ConditionsOperation in experiment
68% With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃; Example 456-(5-Hydroxymethyl-3-pyridin-2-yl-isoxazol-4-ylmethoxy)-N-(tetrahydrofuran-3-yl)-nicotinamide; To a solution of 6-(5-hydroxymethyl-3-pyridin-2-yl-isoxazol-4-ylmethoxy)-nicotinic acid (70 mg, 0.21 mmol) in DMF (5 mL) was added <strong>[88675-24-5]3-aminotetrahydrofuran</strong> (26 mg, 0.30 mmol), N,N,N',N'-tetramethyl-O-(benzotriazole-1-yl)-uronium tetrafluoroborate (96 mg, 0.30 mmol) and N,N-diisopropyl ethylamine (0.15 mL, 0.84 mmol). The reaction mixture was stirred overnight at room temperature. After evaporation of the solvent the residue was partitioned (ethyl acetate/aqueous saturated sodium bicarbonate solution) and the organic phase was dried (Na2SO4) and concentrated. Chromatography (silica, dichloromethane:methanol=100:0 to 97:3) afforded the title compound (58 mg, 68percent) as a colorless oil. MS: m/e=397.1 [M+H]+.
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