138116-34-4|(4-Aminopyridin-3-yl)methanol| Ambeed

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Structure of 138116-34-4

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Quality Control of [ 138116-34-4 ] Purity: 95% SDS Specification

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Product Details of [ 138116-34-4 ]

CAS No. :	138116-34-4
Formula :	C₆H₈N₂O
M.W :	124.14
SMILES Code :	OCC1=C(N)C=CN=C1
MDL No. :	MFCD06203066
InChI Key :	WNBVEYMTVDMSFZ-UHFFFAOYSA-N
Pubchem ID :	10796739

Safety of [ 138116-34-4 ]

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

Computational Chemistry of [ 138116-34-4 ] Show Less

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 ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	59.14 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.01
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	-0.16
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	0.01
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	-0.75
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	0.49
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	0.12

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-0.94
Solubility	14.4 mg/ml ; 0.116 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-0.63
Solubility	29.3 mg/ml ; 0.236 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-1.45
Solubility	4.39 mg/ml ; 0.0354 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	No
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	No
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-7.17 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	1.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	0.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	1.07

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 ]

References: [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 ]

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

[ 138116-34-4 ] Synthesis Path-Downstream 1~21

1
[ 16135-36-7 ]
[ 138116-34-4 ]

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

2
[ 138116-34-4 ]
4-hydroxy-3-hydroxymethylpyridine [ No CAS ]

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

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

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

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

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

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

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

6
[ 7418-65-7 ]
[ 138116-34-4 ]

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

7
[ 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%).

References: [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.

8
[ 138116-34-4 ]
[ 1026039-69-9 ]

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

9
[ 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.

References: [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.

10
[ 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%).

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

11
[ 504-24-5 ]
[ 138116-34-4 ]