Water → methyl 2-[(3S,4R)-4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}-3-(prop-2-en-1-yloxy)piperidin-1-yl]-4-(1-methyl-1H-1,2,4-triazol-5-yl)-1,3-thiazole-5-carboxylate

HRID 655733노트

반응식

HRID 655733 반응식
Cl[C:2]1[S:3][C:4]([C:13]([O:15][CH3:16])=[O:14])=[C:5]([C:7]2[N:11]([CH3:12])[N:10]=[CH:9][N:8]=2)[N:6]=1.[Cl:17][C:18]1[C:22]([Cl:23])=[C:21]([CH3:24])[NH:20][C:19]=1[C:25]([NH:27][C@@H:28]1[CH2:33][CH2:32][NH:31][CH2:30][C@@H:29]1[O:34][CH2:35][CH:36]=[CH2:37])=[O:26].C(N(CC)C(C)C)(C)C.O>CN1CCCC1=O>[Cl:17][C:18]1[C:22]([Cl:23])=[C:21]([CH3:24])[NH:20][C:19]=1[C:25]([NH:27][C@@H:28]1[CH2:33][CH2:32][N:31]([C:2]2[S:3][C:4]([C:13]([O:15][CH3:16])=[O:14])=[C:5]([C:7]3[N:11]([CH3:12])[N:10]=[CH:9][N:8]=3)[N:6]=2)[CH2:30][C@@H:29]1[O:34][CH2:35][CH:36]=[CH2:37])=[O:26]

참가 물질

6

반응물 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 59208415Methyl 2-chloro-4-(1-methyl-1H-1,2,4-triazol-5-yl)-1,3-thiazole-5-carboxylate2회HCID 594024493,4-dichloro-5-methyl-N-[(3S,4R)-3-(prop-2-en-1-yloxy)piperidin-4-yl]-1H-pyrrole-2-carboxamide2회

생성물 1

HCID 46234299methyl 2-[(3S,4R)-4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}-3-(prop-2-en-1-yloxy)piperidin-1-yl]-4-(1-methyl-1H-1,2,4-triazol-5-yl)-1,3-thiazole-5-carboxylate수율 70%

시약·촉매·용매 1

HCID 13387N-methyl-2-pyrrolidone용매

반응 조건

온도
80 °C

실험 절차

Methyl 2-chloro-4-(1-methyl-1H-1,2,4-triazol-5-yl)-1,3-thiazole-5-carboxylate (Intermediate 2, 77.91 mg, 3.02 mmol) was added to a solution of 3,4-dichloro-5-methyl-N-[(3S,4R)-3-(prop-2-en-1-yloxy)piperidin-4-yl]-1H-pyrrole-2-carboxamide (Intermediate 20, 100 mg, 3.02 mmol) and N,N-diisopropylethylamine (0.362 mL, 0.06 mM) in N-methyl 2-pyrrolidinone (1.5 mL) and the resulting reaction mixture was stirred overnight at 80° C. The reaction mixture was cooled to room temperature and poured into water (20 mL). The solid that formed was collected by filtration, washed with diethylether (25 mL) and dried to afford Methyl 2-[(3S,4R)-4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}-3-(prop-2-en-1-yloxy)piperidin-1-yl]-4-(1-methyl-1H-1,2,4-triazol-5-yl)-1,3-thiazole-5-carboxylate (90 mg, 70%) as solid.

후처리

  1. customthe resulting reaction mixture
  2. temperatureThe reaction mixture was cooled to room temperature
  3. customThe solid that formed
  4. filtrationwas collected by filtration
  5. washwashed with diethylether (25 mL)
  6. customdried

출처 및 근거

ORD 기록
ord-94a92ec444fc4d4e830007335bd6d718
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08071605B2

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