4774-10-1|3-Methoxypyrazin-2-amine| Ambeed

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Quality Control of [ 4774-10-1 ] Purity: 98% SDS Specification

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Product Details of [ 4774-10-1 ]

CAS No. :	4774-10-1
Formula :	C₅H₇N₃O
M.W :	125.13
SMILES Code :	NC1=NC=CN=C1OC
MDL No. :	MFCD05722793
InChI Key :	MTMGQKFGZHMTTK-UHFFFAOYSA-N
Pubchem ID :	12489851

Safety of [ 4774-10-1 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Computational Chemistry of [ 4774-10-1 ] Show Less

Physicochemical Properties

Num. heavy atoms	9
Num. arom. heavy atoms	6
Fraction Csp3	0.2
Num. rotatable bonds	1
Num. H-bond acceptors	3.0
Num. H-bond donors	1.0
Molar Refractivity	32.93
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	61.03 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.5
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	-0.26
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	0.08
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.	-0.9
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	0.2
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.	-0.88
Solubility	16.5 mg/ml ; 0.132 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.	-0.56
Solubility	34.2 mg/ml ; 0.274 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	-1.38
Solubility	5.24 mg/ml ; 0.0419 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.	-7.25 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)	2.33

Application In Synthesis of [ 4774-10-1 ]

* 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 [ 4774-10-1 ]

[ 4774-10-1 ] Synthesis Path-Downstream 1~35

1
[ 67-56-1 ]
[ 6863-73-6 ]
[ 4774-10-1 ]

References: [1]Journal of Heterocyclic Chemistry,1990,vol. 27,p. 1639 - 1643.
[2]MedChemComm,2014,vol. 5,p. 333 - 337.

2
[ 15568-85-1 ]
[ 4774-10-1 ]
[ 132973-02-5 ]

References: [1]Journal of Heterocyclic Chemistry,1990,vol. 27,p. 1639 - 1643.

3
[ 13176-46-0 ]
[ 4774-10-1 ]
ethyl 8-methoxyimidazo<1,2-a>pyrazine-2-acetate [ No CAS ]

References: [1]Farmaco, Edizione Scientifica,1981,vol. 36,p. 61 - 80.

4
[ 54260-84-3 ]
[ 4774-10-1 ]
[ 144294-23-5 ]
[ 144294-32-6 ]
[ 144294-31-5 ]

References: [1]Il Farmaco,1992,vol. 47,p. 919 - 930.

5
[ 1074-12-0 ]
[ 4774-10-1 ]
[ 146070-60-2 ]

References: [1]Heterocycles,1992,vol. 34,p. 2065 - 2077.

6
[ 55919-47-6 ]
[ 4774-10-1 ]
[ 144294-16-6 ]

References: [1]Il Farmaco,1992,vol. 47,p. 919 - 930.

7
[ 4774-10-1 ]
[ 152559-46-1 ]
ethyl 2-(4'-chlorophenyl)-8-methoxyimidazo<1,2-a>pyrazine-3-carboxylate [ No CAS ]

References: [1]European Journal of Medicinal Chemistry,1993,vol. 28,p. 337 - 346.

8
[ 4774-10-1 ]
[ 609-15-4 ]
[ 97678-10-9 ]

References: [1]European Journal of Medicinal Chemistry,1985,vol. 20,p. 79 - 85.

9
[ 4774-10-1 ]
[ 87-13-8 ]
[ 132973-00-3 ]

References: [1]Journal of Heterocyclic Chemistry,1990,vol. 27,p. 1639 - 1643.

10
[ 4774-10-1 ]
[ 78-98-8 ]
3,8-dihydroxy-2-methylimidazo<1,2-a>pyrazine [ No CAS ]

References: [1]Heterocycles,1992,vol. 34,p. 2065 - 2077.

11
[ 180284-25-7 ]
[ 4774-10-1 ]

References: [1]Synthesis,1996,p. 838 - 842.

12
[ 4774-10-1 ]
[ 39225-30-4 ]
Ethyl 8-methoxy-2-phenylimidazo<1,2-a>pyrazine-3-acetate [ No CAS ]

References: [1]Monatshefte fur Chemie,1996,vol. 127,p. 947 - 953.

14
[ 3149-28-8 ]
[ 4774-10-1 ]

References: [1]Synthesis,1996,p. 838 - 842.

15
[ 180284-23-5 ]
[ 4774-10-1 ]

References: [1]Synthesis,1996,p. 838 - 842.

16
[ 4774-10-1 ]
[ 144294-26-8 ]

References: [1]Il Farmaco,1992,vol. 47,p. 919 - 930.

17
[ 4774-10-1 ]
[ 144294-19-9 ]

References: [1]Il Farmaco,1992,vol. 47,p. 919 - 930.

18
[ 4774-10-1 ]
[ 132973-06-9 ]

References: [1]Journal of Heterocyclic Chemistry,1990,vol. 27,p. 1639 - 1643.

19
[ 24622-15-9 ]
[ 4774-10-1 ]
[ 809239-73-4 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium tert-butylate; In tetrahydrofuran; at 0 - 20℃; for 2h;	A solution of <strong>[4774-10-1]3-methoxypyrazin-2-amine</strong> (3.5 g) and the product from step (a) (8.0g) in drytetrahydrofuran (35 ml) was treated with potassium f-butoxide (1 M solution intetrahydrofuran, 62 ml), dropwise at 0C, under a nitrogen atmosphere. The brownsuspension was allowed to warm to room temperature over 2 hours and was then pouredinto 2 M hydrochloric acid and extracted into ethyl acetate. The combined organic extractswere purified on a pad of flash silica which was eluted with ethyl acetate. Concentrationof the solvent afforded the titled compound as a brown powder (8.4 g). m/e 374/376 (M-l)', 100percent.JH NMR (D6-DMSO) 5 7.79 (1H, br), 7.69 (1H, br), 3.92 (3H, s).MP 212-214C.Elemental Analysis:Theory: C 28.85, H 1.61, N 11.22 percentFound: C 28.72, H 1.88, N 11.23 percent

References: [1]Patent: WO2004/108717,2004,A1 .Location in patent: Page 18-19.

20
[ 1355999-71-1 ]
[ 4774-10-1 ]
[ 1447364-30-8 ]

Yield	Reaction Conditions	Operation in experiment
1.1 g	With triethylamine; In N,N-dimethyl-formamide; at 100℃; for 3h;	Step 5: ferf-Butyl {1-[4-(8-methoxy-3-phenylimidazo[1,2-a]pyrazin-2- yl)phenyl]cyclobutyl}carbamate [lnt-1 ] A mixture of crude fert-butyl (1-{4-[bromo(phenyl)acetyl]phenyl}cyclobutyl)- carbamate [lnt-1-A] (740 mg, 1.67 mmol, 1.0 eq), <strong>[4774-10-1]3-methoxypyrazin-2-amine</strong> (CAS-Nr. 4774-10-1 , 417 mg, 3.33 mmol, 2 eq), triethylamine (0.35 mL, 2.50 mmol, 1.5 eq) was dissolved in 24 mL DMF and was heated at 100 for 3 hours. On cooling, the mixture was partitioned between ethyl acetate and water, stirred vigorously and the organic phase then was filtered through a silicone coated filter paper. The filtrate was concentrated in vacuo. The crude mixture gave 1.10 g (56percent yield) raw product that contained the title compound in 37percent purity (UPLC, area-percent). The material was forwarded to the next stept without further purification. UPLC-MS (Method 1): RT = 1.47 min; m/z = 471 (M+H) +.

References: [1]Patent: WO2013/104610,2013,A1 .Location in patent: Page/Page column 50.

21
[ 4774-10-1 ]
[ 121-60-8 ]
[ 655-78-7 ]

References: [1]Crystal Growth and Design,2013,vol. 13,p. 4002 - 4016.
[2]MedChemComm,2014,vol. 5,p. 333 - 337.

22
[ 4774-10-1 ]
[ 121-60-8 ]
[ 152-47-6 ]

References: [1]Crystal Growth and Design,2013,vol. 13,p. 4002 - 4016.

23
[ 109-02-4 ]
[ 1398752-23-2 ]
[ 4774-10-1 ]
[ 1398752-43-6 ]

Yield	Reaction Conditions	Operation in experiment
51%	In N,N-dimethyl-formamide; acetonitrile;	Part A (3S)-2-[(2R)-3-Cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoyl]-1-methyl-N-[3-(methyloxy)-2-pyrazinyl]-3-pyrazolidine carboxamide 4-Methylmorpholine (47.4 mul, 0.431 mmol) was added into a solution of (3S)-2-[(2R)-3-cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoyl]-1-[(phenylmethyl)oxy]carbonyl}-3-pyrazolidinecarboxylic acid (150 mg, 0.359 mmol) and 4-[4,6-bis(methyloxy)-1,3,5-triazin-2-yl]-4-methylmorpholin-4-ium (141 mg, 0.431 mmol) in acetonitrile (5.94 ml). The resulting solution was cooled to 0° C. and stirred at 0° C. for 15 min. To the reaction mixture was added <strong>[4774-10-1]3-(methyloxy)-2-pyrazinamine</strong> (67.4 mg, 0.539 mmol). The reaction mixture was stirred for 2 days at rt. The reaction mixture was concentrated in vacuo and the residue was dissolved in DCM, washed with saturated NaHCO3 solution, followed by brine. The solution was dried over sodium sulfate and filtered. The solvent was removed to give a residue which was redissolved in DMF (3.75 ml) and purified by RP-HPLC to afford (3S)-2-[(2R)-3-cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoyl]-1-methyl-N-[3-(methyloxy)-2-pyrazinyl]-3-pyrazolidine carboxamide (96 mg, 0.183 mmol, 51percent yield) as a white solid. LC-MS (ES) m/e 525.5 (M+H)+.

References: [1]Patent: US2013/345120,2013,A1 .Location in patent: Page/Page column.

24
[ 1398752-23-2 ]
[ 4774-10-1 ]
[ 1398751-11-5 ]

References: [1]Patent: US8901119,2014,B2 .
[2]Patent: US2013/345120,2013,A1 .

25
[ 4774-10-1 ]
[ 1398751-45-5 ]

Yield	Reaction Conditions	Operation in experiment
		A procedure similar to Example 59 (Method B), Parts A and B was used, except that <strong>[4774-10-1]3-(methyloxy)-2-pyrazinamine</strong> (52.4 mg, 0.419 mmol) was used instead of 4-pyrimidinamine to add to the reaction mixture in Part A, to provide the Title compound. MS (ES+) m/z 420.8 (MH+). 1H NMR (400 MHz, METHANOL-d4) delta ppm 1.04-1.21 (m, 2H) 1.36-1.63 (m, 5H) 1.70-1.91 (m, 4H) 2.30-2.44 (m, 1H) 2.44-2.55 (m, 1H) 2.82-2.98 (m, 1H) 3.20-3.29 (m, 1H) 3.51 (dd, J=14.02, 4.42 Hz, 1H) 3.59-3.86 (m, 1H) 3.96 (td, J=9.47, 4.80 Hz, 1H) 4.03 (s, 3H) 4.79-4.87 (m, 1H) 7.79-7.94 (m, 2.7H) 8.26 (s, 0.3H)

References: [1]Patent: US2013/345120,2013,A1 .Location in patent: Page/Page column.

26
[ 6863-73-6 ]
[ 4774-10-1 ]

Yield	Reaction Conditions	Operation in experiment
59%	With sodium methylate; In methanol;	Pre Step A 3-(Methyloxy)-2-pyrazinamine A mixture of 3-chloro-2-pyrazinamine (200 mg, 1.544 mmol) and sodium methoxide (250 mg, 4.63 mmol) in methanol (3.9 ml) was heated to 130° C. via a microwave reactor for 60 min. The crude product mixture was purified by RP-HPLC to give 3-(methyloxy)-2-pyrazinamine (113 mg, 0.903 mmol, 59percent yield). MS (ES+) m/z 125.8 (MH+).

References: [1]Patent: US2013/345120,2013,A1 .Location in patent: Page/Page column.

27
[ 4774-10-1 ]
[ 152-47-6 ]