Hydrochloric Acid → [4-((S)-1-amino-3-methyl-butyl)-thiazol-2-yl]-[3-methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-amine trihydrochloride

HRID 604895노트

반응식

HRID 604895 반응식
C(OC(=O)[NH:7][C@H:8]([C:13]1[N:14]=[C:15]([NH:18][C:19]2[CH:24]=[CH:23][C:22]([N:25]3[CH:29]=[C:28]([CH3:30])[N:27]=[CH:26]3)=[C:21]([O:31][CH3:32])[CH:20]=2)[S:16][CH:17]=1)[CH2:9][CH:10]([CH3:12])[CH3:11])(C)(C)C.[ClH:34]>C(Cl)Cl.C(OCC)C>[ClH:34].[ClH:34].[ClH:34].[NH2:7][C@H:8]([C:13]1[N:14]=[C:15]([NH:18][C:19]2[CH:24]=[CH:23][C:22]([N:25]3[CH:29]=[C:28]([CH3:30])[N:27]=[CH:26]3)=[C:21]([O:31][CH3:32])[CH:20]=2)[S:16][CH:17]=1)[CH2:9][CH:10]([CH3:11])[CH3:12]

참가 물질

5

반응물 2

HCID 313Hydrochloric AcidHCID 86624688((S)-1-{2-[3-Methoxy-4-(4-methyl-imidazol-1-yl)-phenylamino]-thiazol-4-yl}-3-methyl-butyl)-carbamic acid tert-butyl ester

생성물 1

HCID 86624689[4-((S)-1-amino-3-methyl-butyl)-thiazol-2-yl]-[3-methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-amine trihydrochloride수율 100%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 6344Dichloromethane용매

실험 절차

1162 mg (2.46 mmol) ((S)—1-{2-[3-Methoxy-4-(4-methyl-imidazol-1-yl)-phenylamino]-thiazol-4-yl}-3-methyl-butyl)-carbamic acid tert-butyl ester was dissolved in methylene chloride (24.6 ml) and 2M HCl in diethyl ether (12.3 ml) was added at room temperature. A solid precipitated. The reaction was stirred at room temperature over night. The reaction was diluted with diethyl ether, stirred for 15 minutes and the solid was filtered off, washed with diethyl ether and dried to yield 1195 mg (100%) [4-((S)-1-amino-3-methyl-butyl)-thiazol-2-yl]-[3-methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-amine trihydrochloride as a light yellow solid. MS ISP (m/e): 372.2 (100) (M+H)+. 1H NMR (DMSO-D6, 250 MHz): δ (ppm)=10.98 (s, 1H), 9.31 (s, 1H), 8.46 (br s, 3H), 7.93 (s, 1H), 7.66 (s, 1H), 7.47 (d, 1H), 7.31 (d, 1H), 7.13 (s, 1H), 4.27 (m, 1H), 3.90 (s, 3H), 2.35 (s, 3H), 1.94-1.83 (m, 1H), 1.80-1.69 (m, 1H), 1.52-1.39 (m, 1H), 0.90 (d, 3H), 0.86 (d, 3H).

후처리

  1. customA solid precipitated
  2. additionThe reaction was diluted with diethyl ether
  3. stirringstirred for 15 minutes
  4. filtrationthe solid was filtered off
  5. washwashed with diethyl ether
  6. customdried

출처 및 근거

ORD 기록
ord-66f0e71b6d5c415e8c29baf017805c62
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07910740B2

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