Ethanol → {3-Amino-6-[2-methyl-5-(morpholine-4-sulfonyl)-phenyl]-pyrazin-2-yl}-pyridin-3-yl-methanone O-methyl-oxime

HRID 81467Notes

Reaction equation

HRID 81467 reaction equation
[NH2:1][C:2]1[C:3]([C:24]([C:26]2[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=2)=O)=[N:4][C:5]([C:8]2[CH:13]=[C:12]([S:14]([N:17]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)(=[O:16])=[O:15])[CH:11]=[CH:10][C:9]=2[CH3:23])=[CH:6][N:7]=1.Cl.[CH3:33][O:34][NH2:35].C(O)C.C(N(CC)CC)C>O>[CH3:33][O:34][N:35]=[C:24]([C:3]1[C:2]([NH2:1])=[N:7][CH:6]=[C:5]([C:8]2[CH:13]=[C:12]([S:14]([N:17]3[CH2:18][CH2:19][O:20][CH2:21][CH2:22]3)(=[O:16])=[O:15])[CH:11]=[CH:10][C:9]=2[CH3:23])[N:4]=1)[C:26]1[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 8471TriethylamineHCID 521874O-Methylhydroxylamine hydrochlorideHCID 44235791{3-Amino-6-[2-methyl-5-(morpholine-4-sulfonyl)-phenyl]-pyrazin-2-yl}-pyridin-3-yl-methanone

Product 1

HCID 74960526{3-Amino-6-[2-methyl-5-(morpholine-4-sulfonyl)-phenyl]-pyrazin-2-yl}-pyridin-3-yl-methanone O-methyl-oxime

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

{3-Amino-6-[2-methyl-5-(morpholine-4-sulfonyl)-phenyl]-pyrazin-2-yl}-pyridin-3-yl-methanone (Ex. 2) (0.05 g, 0.11 mmol), O-methylhydroxylamine hydrochloride (0.095 g, 1.14 mmol), ethanol (4 ml), water (1 ml) and triethylamine (0.07 g, 0.68 mmol) are heated at 120° C. in a microwave for 3.5 hours. The reaction mixture is purified by reverse phase column chromatography (C18, 0-100% MeCN in water −0.1% TFA) to yield the title compound. 1H NMR (400 MHz, DMSO-6) δ 8.56 (1H, dd), 8.48 (1H, d), 8.35 (1H, s), 7.75 (1H, dt), 7.70 (2H, bs), 7.55-7.53 (2H, m), 7.48-7.43 (2H, m), 4.01 (3H, s), 3.61 (4H, t), 2.76 (4H, t) 2.19 (3H, s); MS m/z 469 [M+H]+

Workup

  1. customThe reaction mixture is purified by reverse phase column chromatography (C18, 0-100% MeCN in water −0.1% TFA)

Sources & evidence

ORD record
ord-c7fdecf6018e40c2aaa7ddbe3c3168de
Source dataset
uspto-grants-2014_09
Patent number
US08846687B2

Reaction notes

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