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 1667704노트

반응식

HRID 1667704 반응식
[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]

참가 물질

5

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 23994Zinc촉매3회HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-ec1f5a2f2bd54ab092d3bae508807d2c
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08044213B2

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