2-Aminothiazole → HCID 178500665, 화합물

HRID 1713752노트

반응식

HRID 1713752 반응식
[C:1](C1NC=CN=1)(C1NC=CN=1)=S.[NH2:13][C:14]1[S:15][CH:16]=[CH:17][N:18]=1.[NH:19]([C:21](=[O:42])[C:22]([NH:24][C:25]1[CH:30]=[CH:29][C:28]([C@H:31]2[CH2:36][CH2:35][C@H:34]([CH2:37][C:38]([O:40][CH3:41])=[O:39])[CH2:33][CH2:32]2)=[CH:27][CH:26]=1)=[O:23])[NH2:20].CCN=C=NCCCN(C)C>CC(N(C)C)=O.O>[S:15]1[CH:16]=[CH:17][N:18]=[C:14]1[NH:13][C:1]1[O:42][C:21]([C:22]([NH:24][C:25]2[CH:26]=[CH:27][C:28]([C@H:31]3[CH2:32][CH2:33][C@H:34]([CH2:37][C:38]([O:40][CH3:41])=[O:39])[CH2:35][CH2:36]3)=[CH:29][CH:30]=2)=[O:23])=[N:19][N:20]=1

참가 물질

7

반응물 4

HCID 21552-AminothiazoleHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 11412697Thiocarbonyl diimidazoleHCID 178500682HCID 178500682, 화합물2회

생성물 1

HCID 178500665HCID 178500665, 화합물수율 36.8%

시약·촉매·용매 2

HCID 962Water용매HCID 31374Dimethylacetamide용매

실험 절차

Thiocarbonyl diimidazole (179 mg, 1.00 mmol) was added in one portion to a solution of 2-aminothiazole (100 mg, 1.00 mmol) in DMA (5 mL) and the solution was stirred at room temperature for 6 h. Methyl [trans-4-(4-{[hydrazino(oxo)acetyl]amino}phenyl)cyclohexyl]-acetate (Intermediate 43, 267 mg, 0.80 mmol) was added in one portion and the reaction mixture was stirred at room temperature for 20 h and then heated at 80° C. for 10 minutes in the microwave. The solution was cooled to room temperature and EDCI (192 mg, 1.00 mmol) was added in one portion and the reaction mixture was heated to 90° C. for 15 minutes in the microwave. The reaction mixture was cooled to room temperature and poured into water (200 mL). The mixture was filtered and the resulting solid was recrystallised (CH3CN) to give the title compound (130 mg, 29%) as a solid; 1H NMR δ 1.09-1.18 (2H, m), 1.42-1.47 (2H, m), 1.79 (5H, m), 2.24-2.26 (2H, d), 2.45 (1H, t), 3.61 (3H, s), 6.99 (1H, d), 7.22 (2H, d), 7.38 (1H, d), 7.67-7.70 (2H, m), 10.78 (1H, s);

후처리

  1. stirringthe reaction mixture was stirred at room temperature for 20 h
  2. temperatureheated at 80° C. for 10 minutes in the microwave
  3. temperatureThe solution was cooled to room temperature
  4. temperaturethe reaction mixture was heated to 90° C. for 15 minutes in the microwave
  5. temperatureThe reaction mixture was cooled to room temperature
  6. filtrationThe mixture was filtered
  7. customthe resulting solid was recrystallised (CH3CN)

출처 및 근거

ORD 기록
ord-42b4f57e748745ec88bdc689054f5203
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07795283B2

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