2-Aminothiazole → 4-Cyclohexyl-4-(thiazol-2-ylaminomethyl)-piperidine-1-carboxylic acid tert-butyl ester

HRID 1795172노트

반응식

HRID 1795172 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)([CH:14]=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:22][C:23]1[S:24][CH:25]=[CH:26][N:27]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C1(C)C=CC=CC=1.C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)([CH2:14][NH:22][C:23]2[S:24][CH:25]=[CH:26][N:27]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

참가 물질

6

반응물 3

HCID 21552-AminothiazoleHCID 5049666Sodium triacetoxyborohydrideHCID 219368754-Cyclohexyl-4-formylpiperidine-1-carboxylic acid tert-butyl ester

생성물 1

HCID 210237784-Cyclohexyl-4-(thiazol-2-ylaminomethyl)-piperidine-1-carboxylic acid tert-butyl ester수율 82%

시약·촉매·용매 2

HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

실험 절차

4-Cyclohexyl-4-formyl-piperidine-1-carboxylic acid tert-butyl ester, 3, (296 mg, 1.0 mmol) and 2-aminothiazole (103 mg, 1.0 mmol) are dissolved in toluene (15 mL), and the mixture was refluxed using a Dean-Stark apparatus overnight. The solution is then cooled to room temperature and sodium triacetoxyborohydride added. The reaction is stirred at room temperature for three hours and then diluted with ethyl acetate. The reaction mixture is washed with aqueous sodium bicarbonate and brine. The solvent is removed under reduced pressure and the residue purified by preparative HPLC to afford 312 mg (82% yield) of the desired compound. MS (ESI) m/z 380 (M+H+)

후처리

  1. temperaturethe mixture was refluxed
  2. customa Dean-Stark apparatus overnight
  3. washThe reaction mixture is washed with aqueous sodium bicarbonate and brine
  4. customThe solvent is removed under reduced pressure
  5. customthe residue purified by preparative HPLC

출처 및 근거

ORD 기록
ord-33eec37674764f2fa0152207c7eb01cc
출처 데이터셋
uspto-grants-2006_04
특허 번호
US07026335B2

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