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

HRID 1713904노트

반응식

HRID 1713904 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-494f2ad5a3034f4d83271e16b5fb64b2
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07795283B2

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