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 655733ノート

反応式

HRID 655733 の反応式
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]

参加物

6

反応物 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 59208415Methyl 2-chloro-4-(1-methyl-1H-1,2,4-triazol-5-yl)-1,3-thiazole-5-carboxylate2 回HCID 594024493,4-dichloro-5-methyl-N-[(3S,4R)-3-(prop-2-en-1-yloxy)piperidin-4-yl]-1H-pyrrole-2-carboxamide2 回

生成物 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-carboxylate収率 70%

試薬・触媒・溶媒 1

HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
80 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-94a92ec444fc4d4e830007335bd6d718
出典データセット
uspto-grants-2011_12
特許番号
US08071605B2

反応ノート

読み込み中…