[ CAS No. 138116-34-4 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}

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Quality Control of [ 138116-34-4 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 138116-34-4 ]

SDS Specification

Alternatived Products of [ 138116-34-4 ]

Product Details of [ 138116-34-4 ]

CAS No. :	138116-34-4	MDL No. :	MFCD06203066
Formula :	C₆H₈N₂O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	WNBVEYMTVDMSFZ-UHFFFAOYSA-N
M.W :	124.14	Pubchem ID :	10796739
Synonyms :

Calculated chemistry of [ 138116-34-4 ] Expand+

Physicochemical Properties

Num. heavy atoms :	9
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.17
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	2.0
Molar Refractivity :	34.77
TPSA :	59.14 ?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) :	-7.17 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.01
Log Po/w (XLOGP3) :	-0.16
Log Po/w (WLOGP) :	0.01
Log Po/w (MLOGP) :	-0.75
Log Po/w (SILICOS-IT) :	0.49
Consensus Log Po/w :	0.12

Druglikeness

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

Water Solubility

Log S (ESOL) :	-0.94
Solubility :	14.4 mg/ml ; 0.116 mol/l
Class :	Very soluble
Log S (Ali) :	-0.63
Solubility :	29.3 mg/ml ; 0.236 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.45
Solubility :	4.39 mg/ml ; 0.0354 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.07

Safety of [ 138116-34-4 ]

Signal Word:	Danger	Class:	6.1
Precautionary Statements:	P261-P264-P301+P310+P330-P305+P351+P338	UN#:	2811
Hazard Statements:	H300-H315-H319-H335-H411	Packing Group:	Ⅱ
GHS Pictogram:

Application In Synthesis of [ 138116-34-4 ]

* 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.

Upstream synthesis route of [ 138116-34-4 ]
Downstream synthetic route of [ 138116-34-4 ]

[ 138116-34-4 ] Synthesis Path-Upstream 1~9

1
[ 42373-30-8 ]
[ 138116-34-4 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 6, p. 2206 - 2210
[2] Patent: WO2013/13817, 2013, A1, . Location in patent: Page/Page column 144
[3] Patent: US2013/29961, 2013, A1, . Location in patent: Paragraph 0818

2
[ 16135-36-7 ]
[ 138116-34-4 ]

Reference： [1] Synthetic Communications, 1996, vol. 26, # 12, p. 2257 - 2272

3
[ 1003-73-2 ]
[ 138116-34-4 ]

Reference： [1] Synthetic Communications, 1996, vol. 26, # 12, p. 2257 - 2272

4
[ 1074-98-2 ]
[ 138116-34-4 ]

Reference： [1] Synthetic Communications, 1996, vol. 26, # 12, p. 2257 - 2272

5
[ 1078-05-3 ]
[ 138116-34-4 ]

Reference： [1] Synthetic Communications, 1996, vol. 26, # 12, p. 2257 - 2272

6
[ 504-24-5 ]
[ 138116-34-4 ]

Reference： [1] Patent: WO2013/13817, 2013, A1,
[2] Patent: US2013/29961, 2013, A1,

7
[ 70298-89-4 ]
[ 138116-34-4 ]

Reference： [1] Patent: WO2013/13817, 2013, A1,
[2] Patent: US2013/29961, 2013, A1,

8
[ 86847-71-4 ]
[ 138116-34-4 ]

Reference： [1] Patent: WO2013/13817, 2013, A1,
[2] Patent: US2013/29961, 2013, A1,

9
[ 7418-65-7 ]
[ 138116-34-4 ]

Reference： [1] Synthetic Communications, 1996, vol. 26, # 12, p. 2257 - 2272

[ 138116-34-4 ] Synthesis Path-Downstream 1~13

1
[ 1003-73-2 ]
[ 138116-34-4 ]

Reference： [1]Synthetic Communications,1996,vol. 26,p. 2257 - 2272

2
[ 1074-98-2 ]
[ 138116-34-4 ]

Reference： [1]Synthetic Communications,1996,vol. 26,p. 2257 - 2272

3
[ 1078-05-3 ]
[ 138116-34-4 ]

Reference： [1]Synthetic Communications,1996,vol. 26,p. 2257 - 2272

4
[ 7418-65-7 ]
[ 138116-34-4 ]

Reference： [1]Synthetic Communications,1996,vol. 26,p. 2257 - 2272

5
[ 42373-30-8 ]
[ 138116-34-4 ]

Yield	Reaction Conditions	Operation in experiment
	With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 20℃; for 0.5h;	A solution of 4-aminonicotinaldehyde (57 mg, 0.47 mmol) in tetrahydrofuran was cooled in an ice bath and lithium aluminium hydride (27 mg, 0.70 mmol, 1.5 eq) was added. The ice bath was removed and the reaction mixture was sittred for 30 min. TLC showed complete consumption of starting material. The reaction mixture was quenched with water (1 mL) and 1 N HCI (2 mL) was added extracted with ethylacetate. The organic part was washed with water and brine. The organic layer was dried over MgS04 and concentrated under reduced pressure. The residue was used for the next reaction with in a crude state (60 mg, 99 %).
	With lithium aluminium tetrahydride; In tetrahydrofuran; for 0.5h;Cooling with ice;	Step 4: A solution of 4-aminonicotinaldehyde (57 mg, 0.47 mmol) in tetrahydrofuran was cooled in an ice bath and lithium aluminium hydride (27 mg, 0.70 mmol, 1.5 eq) was added. The ice bath was removed and the reaction mixture was sittred for 30 min. TLC showed complete consumption of starting material. The reaction mixture was quenched with water (1 mL) and 1 N HCl (2 mL) was added extracted with ethylacetate. The organic part was washed with water and brine. The organic layer was dried over MgSO4 and concentrated under reduced pressure. The residue was used for the next reaction with in a crude state (60 mg, 99%).

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 2206 - 2210
[2]Patent: WO2013/13817,2013,A1 .Location in patent: Page/Page column 144
[3]Patent: US2013/29961,2013,A1 .Location in patent: Paragraph 0818

6
[ 138116-34-4 ]
[ 1026039-69-9 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 2206 - 2210

7
[ 1323919-34-1 ]
[ 138116-34-4 ]
[ 1330531-71-9 ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate;tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In 1,4-dioxane; at 90℃; for 18.0h;	150 mg 4-chloro-2-(2-fluoro-5-trifluoromethyl-phenyl)-[1 ,8]naphthyridine and 57 mg<strong>[138116-34-4]4-amino-3-hydroxymethylpyridine</strong> in 6 ml dioxane containing 299 mg Cs2C03) 8 mgPd2(dba)3 and 10 mg xantphos were incubated under argon gas at 90C for 18 hrs. After evaporation to dryness the crude sample was flashed on Si02 with a MeOH gradient in DCM. A pooled fraction was evaporated to give 59 mg product {4-[2-(2-fluoro-5- trifluoromethyl-phenyl)-[1 ,8]naphthyridin-4-ylamino]-pyridin-3-yl}-methanol withRt ~ 1 48 min and correct mass found M+H - 415.
	With caesium carbonate;tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In 1,4-dioxane; at 90℃; for 18.0h;Inert atmosphere;	EXAMPLE 11Synthesis of {4-[2-(2-fluoro-5-trifluoromethyl-phenyl)-[1,8]naphthyridin-4-ylamino]-pyridin-3-yl}-methanol150 mg 4-chloro-2-(2-fluoro-5-trifluoromethyl-phenyl)-[1,8]naphthyridine and 57 mg <strong>[138116-34-4]4-amino-3-hydroxymethylpyridine</strong> in 6 ml dioxane containing 299 mg Cs2CO3, 8 mg Pd2 (dba)3 and 10 mg xantphos were incubated under argon gas at 90 C. for 18 hrs. After evaporation to dryness the crude sample was flashed on SiO2 with a MeOH gradient in DCM. A pooled fraction was evaporated to give 59 mg product {4-[2-(2-fluoro-5-trifluoromethyl-phenyl)-[1,8]naphthyridin-4-ylamino]-pyridin-3-yl}-methanol with Rt1.48 min and correct mass found M+H415.

Reference： [1]Patent: WO2011/101069,2011,A2 .Location in patent: Page/Page column 30; 93
[2]Patent: US2012/316166,2012,A1 .Location in patent: Page/Page column 73

8
[ 18162-48-6 ]
[ 138116-34-4 ]
[ 1421473-35-9 ]

Yield	Reaction Conditions	Operation in experiment
325 mg	With 1H-imidazole; In N,N-dimethyl-formamide; at 20℃; for 5.0h;	To a stirred solution of <strong>[138116-34-4](4-aminopyridin-3-yl)methanol</strong> (200 mg, 1.61 mmol) in dimethylformamide were added imidazole (219 mg, 3.22 mmol, 2 eq) and tert- butyldimethylchlorosilane (267 mg, 1.77 mmol, 1.1 eq). The reaction mixture was stirred at room temperature for 5 h. The mixture was dissolved in ethylacetate and washed with water several times. The organic layer was dried over MgS04 and filtered. The filtrate was removed in vacuo. The crude was purified by column chromatography get 3-((tert- butyldimethylsilyloxy)methyl)pyridin-4-amine (325 mg, 85 %).
325 mg	With 1H-imidazole; In N,N-dimethyl-formamide; at 20℃; for 5.0h;	Step 5: To a stirred solution of <strong>[138116-34-4](4-aminopyridin-3-yl)methanol</strong> (200 mg, 1.61 mmol) in dimethylformamide were added imidazole (219 mg, 3.22 mmol, 2 eq) and tert-butyldimethylchlorosilane (267 mg, 1.77 mmol, 1.1 eq). The reaction mixture was stirred at room temperature for 5 h. The mixture was dissolved in ethylacetate and washed with water several times. The organic layer was dried over MgSO4 and filtered. The filtrate was removed in vacuo. The crude was purified by column chromatography get 3-((tert-butyldimethylsilyloxy)methyl)pyridin-4-amine (325 mg, 85%).

Reference： [1]Patent: WO2013/13817,2013,A1 .Location in patent: Page/Page column 144
[2]Patent: US2013/29961,2013,A1 .Location in patent: Paragraph 0819

9
[ 504-24-5 ]
[ 138116-34-4 ]