Benzoyl chloride → 2-Benzoylamino-4-methylthiazole-5-carboxylic Acid Benzylamide

HRID 45325

반응식

HRID 45325 반응식
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:10]([NH:17][C:18]([C:20]1[S:24][C:23]([NH2:25])=[N:22][C:21]=1[CH3:26])=[O:19])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(N(CC)CC)C>CN(C)C1C=CN=CC=1.O1CCCC1>[CH2:10]([NH:17][C:18]([C:20]1[S:24][C:23]([NH:25][C:1](=[O:8])[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[N:22][C:21]=1[CH3:26])=[O:19])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

참가 물질

6

반응물 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 210824N-Benzyl-2-imino-4-methyl-2,3-dihydro-1,3-thiazole-5-carboximidic acid

생성물 1

HCID 32780072-Benzoylamino-4-methylthiazole-5-carboxylic Acid Benzylamide수율 75%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 8028Tetrahydrofuran용매

실험 절차

Benzoyl chloride (0.04 mL, 0.36 mmol) was added to a mixture of 2-amino-4-methylthiazole-5-carboxylic acid benzylamide (0.083 g, 0.033 mmol), 4-dimethylamino-pyridine (10 mg) and triethylamine (0.06 mL, 0.43 mmol) in tetrahydrofuran (10 mL) at 0° C. The reaction mixture was stirred at ambient temperature for 8 h, then concentrated. The residue was purified by column chromatography to afford the title compound in 75% yield (87 mg); 1H NMR (CDCl3, 300 MHz) δ 7.90-7.24 (m, 11H), 5.97 (s, br, 1H), 4.59 (d, J=5.8 Hz, 2H), 2.45 (s, 3H); MS (ES+) m/z 352.0 (M+1).

후처리

  1. concentrationconcentrated
  2. customThe residue was purified by column chromatography

출처 및 근거

ORD 기록
ord-00ace1ad3c1049e097ce24439e3c84fb
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08541457B2

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