Water → Tert-butyl cis-2-(6-amino-3-chloro-5-(2-phenylpropan-2-ylaminocarbonyl)pyridin-2-ylamino)cyclohexylcarbamate

HRID 2406699노트

반응식

HRID 2406699 반응식
[Cl:1]N1C(=O)CCC1=O.CN(C=O)C.[NH2:14][C:15]1[N:20]=[C:19]([NH:21][C@H:22]2[CH2:27][CH2:26][CH2:25][CH2:24][C@H:23]2[NH:28][C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:33])[CH3:32])[CH:18]=[CH:17][C:16]=1[C:36]([NH:38][C:39]([C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)([CH3:41])[CH3:40])=[O:37].O>C(OCC)(=O)C>[NH2:14][C:15]1[N:20]=[C:19]([NH:21][C@H:22]2[CH2:27][CH2:26][CH2:25][CH2:24][C@H:23]2[NH:28][C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:33])[CH3:32])[C:18]([Cl:1])=[CH:17][C:16]=1[C:36]([NH:38][C:39]([C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)([CH3:40])[CH3:41])=[O:37]

참가 물질

6

반응물 4

HCID 962WaterHCID 6228DimethylformamideHCID 31398ChlorosuccinimideHCID 86683853Tert-butyl cis-2-(6-amino-5-(2-phenylpropan-2-ylaminocarbonyl)pyridin-2-ylamino)cyclohexylcarbamate

생성물 1

HCID 86683895Tert-butyl cis-2-(6-amino-3-chloro-5-(2-phenylpropan-2-ylaminocarbonyl)pyridin-2-ylamino)cyclohexylcarbamate수율 78.2%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

N-chlorosuccinimide (17 mg) was added to a DMF (5 ml) solution containing tert-butyl cis-2-(6-amino-5-(2-phenylpropan-2-ylaminocarbonyl)pyridin-2-ylamino)cyclohexylcarbamate (60 mg) at 0° C., followed by stirring for 1 hour. Water and ethyl acetate were added to the reaction mixture. The organic layer was collected, washed with saturated saline, and dried over anhydrous sodium sulfate, and then the solvent was distilled away under reduced pressure. The obtained residue was purified by silica gel chromatography (silica gel: silica gel 60 (spherical shape) (Kanto Chemical Co., Inc.); hexane:ethyl acetate=3:1), and a white solid of tert-butyl cis-2-(6-amino-3-chloro-5-(2-phenylpropan-2-ylaminocarbonyl)pyridin-2-ylamino)cyclohexylcarbamate (50 mg) was thus obtained.

후처리

  1. customThe organic layer was collected
  2. washwashed with saturated saline
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationthe solvent was distilled away under reduced pressure
  5. customThe obtained residue was purified by silica gel chromatography (silica gel: silica gel 60 (spherical shape) (Kanto Chemical Co., Inc.); hexane:ethyl acetate=3:1)

출처 및 근거

ORD 기록
ord-ed0d84575a1647e590b1db23b260e3a0
출처 데이터셋
uspto-grants-2014_08
특허 번호
US08809371B2

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