Ammonium Chloride → (1-{4-Amino-3-[5-carbamoyl-4-(3-chloro-phenyl)-thiazol-2-ylamino]-benzyl}-piperidin-4-yl)-carbamic acid tert-butyl ester

HRID 1667704ノート

反応式

HRID 1667704 の反応式
[C:1]([O:5][C:6](=[O:40])[NH:7][CH:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-])=O)=[C:17]([NH:24][C:25]3[S:26][C:27]([C:37](=[O:39])[NH2:38])=[C:28]([C:30]4[CH:35]=[CH:34][CH:33]=[C:32]([Cl:36])[CH:31]=4)[N:29]=3)[CH:16]=2)[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[Cl-].[NH4+]>[Zn].O1CCCC1>[C:1]([O:5][C:6](=[O:40])[NH:7][CH:8]1[CH2:9][CH2:10][N:11]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([NH2:21])=[C:17]([NH:24][C:25]3[S:26][C:27]([C:37](=[O:39])[NH2:38])=[C:28]([C:30]4[CH:35]=[CH:34][CH:33]=[C:32]([Cl:36])[CH:31]=4)[N:29]=3)[CH:16]=2)[CH2:12][CH2:13]1)([CH3:4])([CH3:2])[CH3:3]

参加物

5

反応物 2

HCID 25517Ammonium ChlorideHCID 86642815(1-{3-[5-Carbamoyl-4-(3-chloro-phenyl)-thiazol-2-ylamino]-4-nitro-benzyl}-piperidin-4-yl)-carbamic acid tert-butyl ester

生成物 1

HCID 86642816(1-{4-Amino-3-[5-carbamoyl-4-(3-chloro-phenyl)-thiazol-2-ylamino]-benzyl}-piperidin-4-yl)-carbamic acid tert-butyl ester収率 97%

試薬・触媒・溶媒 2

HCID 23994Zinc触媒3 回HCID 8028Tetrahydrofuran溶媒

実験手順

To a suspension of 0.250 g of (1-{3-[5-carbamoyl-4-(3-chloro-phenyl)-thiazol-2-ylamino]-4-nitro-benzyl}-piperidin-4-yl)-carbamic acid tert-butyl ester (VI.12a), 10 mL of tetrahydrofuran, and 10 mL of saturated ammonium chloride solution was added 0.15 g (6.9 mg-atom) of zinc powder. After 15 minutes, another 0.15 g of zinc powder was added. The mixture was stirred for another 10 minutes, then 0.15 g of zinc powder was added. The mixture was filtered, and 30 mL of saturated ammonium chloride solution plus 30 mL of tetrahydrofuran were added to the filtrate. The tetrahydrofuran layer was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give 0.23 g of (1-{4-amino-3-[5-carbamoyl-4-(3-chloro-phenyl)-thiazol-2-ylamino]-benzyl}-piperidin-4-yl)-carbamic acid tert-butyl ester (VII.12), which was used directly in the next step.

後処理

  1. filtrationThe mixture was filtered
  2. addition30 mL of saturated ammonium chloride solution plus 30 mL of tetrahydrofuran were added to the filtrate
  3. dry with materialThe tetrahydrofuran layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-ec1f5a2f2bd54ab092d3bae508807d2c
出典データセット
uspto-grants-2011_10
特許番号
US08044213B2

反応ノート

読み込み中…