Hydrochloric Acid → 4-Methyl-2-[4-(2H-tetrazol-5-yl)benzoylamino]thiazole-5-carboxylic Acid Benzylamide

HRID 45374노트

반응식

HRID 45374 반응식
[CH2:1]([NH:8][C:9]([C:11]1[S:15][C:14]([NH:16][C:17](=[O:26])[C:18]2[CH:23]=[CH:22][C:21]([C:24]#[N:25])=[CH:20][CH:19]=2)=[N:13][C:12]=1[CH3:27])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N-:28]=[N+:29]=[N-:30].[Na+].[Cl-].[NH4+].Cl>CN(C)C=O.[Cl-].[Na+].O.C(OCC)(=O)C>[CH2:1]([NH:8][C:9]([C:11]1[S:15][C:14]([NH:16][C:17](=[O:26])[C:18]2[CH:19]=[CH:20][C:21]([C:24]3[N:28]=[N:29][NH:30][N:25]=3)=[CH:22][CH:23]=2)=[N:13][C:12]=1[CH3:27])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

8

반응물 4

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 593696972-(4-Cyanobenzoylamino)-4-methylthiazole-5-carboxylic Acid Benzylamide

생성물 1

HCID 593696754-Methyl-2-[4-(2H-tetrazol-5-yl)benzoylamino]thiazole-5-carboxylic Acid Benzylamide수율 23%

시약·촉매·용매 3

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매HCID 57417360Sodium chloride; water용매

반응 조건

온도
80 °C

실험 절차

A mixture of 2-(4-cyanobenzoylamino)-4-methylthiazole-5-carboxylic acid benzylamide (0.080 g, 0.21 mmol), sodium azide (0.028 g, 0.43 mmol) and ammonium chloride (0.006 g, 0.11 mmol) in N,N-dimethylformamide (5 mL) was stirred at 80° C. for 18 hours. The reaction mixture was cooled to ambient temperature, and 1 N hydrochloric acid (0.5 mL) solution was added. Ethyl acetate (10 mL) and brine (10 mL) were added to the reaction mixture. The organic layer was separated and dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrate in vacuo and the residue was purified by column chromatography to afford the title compound as a white solid in 23% yield (0.020 g); m.p.>300° C.; 1H NMR (CD3OD, 300 MHz) δ 8.20-8.09 (m, 4H), 8.45-7.20 (m, 5H), 4.51 (s, 2H), 2.55 (s, 3H); 13C NMR (CD3OD, 75 MHz) δ 163.6, 138.8, 128.4, 128.1, 127.1, 126.8, 126.5, 43.1, 15.8; MS (ES+) m/z 420.5 (M+1).

후처리

  1. temperatureThe reaction mixture was cooled to ambient temperature
  2. customThe organic layer was separated
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrate in vacuo
  6. customthe residue was purified by column chromatography

출처 및 근거

ORD 기록
ord-b9b7d9fc42ce4e258a4d6c7ef784513e
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08541457B2

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