Triethylamine → Methyl 1-(5-{[methoxy(oxo)acetyl]amino}pyridin-2-yl)-4-methylpiperidine-4-carboxylate

HRID 1713904ノート

反応式

HRID 1713904 の反応式
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH2:13][CH2:12][C:11]([CH3:18])([C:14]([O:16][CH3:17])=[O:15])[CH2:10][CH2:9]2)=[N:6][CH:7]=1.C(N(CC)CC)C.Cl[C:27](=[O:32])[C:28]([O:30][CH3:31])=[O:29]>C(Cl)Cl>[CH3:31][O:30][C:28](=[O:29])[C:27]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH2:13][CH2:12][C:11]([CH3:18])([C:14]([O:16][CH3:17])=[O:15])[CH2:10][CH2:9]2)=[N:6][CH:7]=1)=[O:32]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 79846Methyl chloroglyoxylateHCID 59464146Methyl 1-(5-aminopyridin-2-yl)-4-methylpiperidine-4-carboxylate

生成物 1

HCID 59464082Methyl 1-(5-{[methoxy(oxo)acetyl]amino}pyridin-2-yl)-4-methylpiperidine-4-carboxylate収率 100%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of methyl 1-(5-aminopyridin-2-yl)-4-methylpiperidine-4-carboxylate (2.96 g, 11.89 mmol) in DCM (100 mL) was added triethylamine (2.2 mL, 15.84 mmol) followed by methyl chlorooxoacetate (1.6 mL, 17.15 mmol) and the reaction mixture was allowed to stir at ambient temperature for 1.5 hrs. The reaction mixture was washed with brine (2×100 mL), the aqueous layer was re extracted with DCM (50 mL) and the organic washings were combined, dried and concentrated to leave the title compound as a brown gum (3.98 g, 11.89 mmol, 100%). 1H NMR (CDCl3) δ 1.72-1.82 (m, 2H), 1.96-2.02 (m, 2H), 2.52-2.59 (m, 1H), 2.95-3.03 (m, 2H), 3.70 (s, 3H), 3.97 (s, 3H), 4.16-4.22 (m, 2H), 6.67 (d, 1H), 7.93 (d, 1H), 8.28 (s, 1H), 8.66 (s, 1H); MS m/e MH+ 336.

後処理

  1. washThe reaction mixture was washed with brine (2×100 mL)
  2. extractionthe aqueous layer was re extracted with DCM (50 mL)
  3. customdried
  4. concentrationconcentrated

出典と根拠

ORDレコード
ord-494f2ad5a3034f4d83271e16b5fb64b2
出典データセット
uspto-grants-2010_09
特許番号
US07795283B2

反応ノート

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