Acetyl chloride → tert-Butyl 4-[5-(2-acetamidopyridin-4-yl)-4-(3-chlorophenyl)-1,3-thiazol-2-yl]piperidine-1-carboxylate

HRID 1727375노트

반응식

HRID 1727375 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[S:15][C:16]([C:26]3[CH:31]=[CH:30][N:29]=[C:28]([NH2:32])[CH:27]=3)=[C:17]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[CH:20]=3)[N:18]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:33](Cl)(=[O:35])[CH3:34].C(N(CC)CC)C.C(=O)([O-])O.[Na+]>O1CCCC1>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([C:14]2[S:15][C:16]([C:26]3[CH:31]=[CH:30][N:29]=[C:28]([NH:32][C:33](=[O:35])[CH3:34])[CH:27]=3)=[C:17]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[CH:20]=3)[N:18]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

참가 물질

6

반응물 4

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 57349380tert-Butyl 4-[5-(2-aminopyridin-4-yl)-4-(3-chlorophenyl)-1,3-thiazol-2-yl]piperidine-1-carboxylate

생성물 1

HCID 57349381tert-Butyl 4-[5-(2-acetamidopyridin-4-yl)-4-(3-chlorophenyl)-1,3-thiazol-2-yl]piperidine-1-carboxylate수율 102.6%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of [4-[2-(1-tert-butoxycarbonylpiperidin-4-yl)-4-(3-chlorophenyl)-1,3-thiazol-5-yl]-2-pyridylamine (1.60 g, 3.40 mmol) in tetrahydrofuran (20 mL) were added acetyl chloride (0.25 mL, 3.52 mmol) and triethylamine (0.50 mL, 3.58 mmol) at 0° C. sequentially, and the resulting mixture was stirred at room temperature for 3 hours. Aqueous sodium hydrogen carbonate was added to the reaction mixture and extracted with ethyl acetate. The extracts were washed with brine, dried, and concentrated. The residue was purified by column chromatography (filler: Chromatorex NH DM1020 (trade name, manufactured by Fuji Silysia Chemical Ltd.), hexane-ethyl acetate=1:1) to give a title compound (1.79 g, yield 98%).

후처리

  1. extractionextracted with ethyl acetate
  2. washThe extracts were washed with brine
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography (filler: Chromatorex NH DM1020 (trade name, manufactured by Fuji Silysia Chemical Ltd.), hexane-ethyl acetate=1:1)

출처 및 근거

ORD 기록
ord-25502566e52048fabecc89ee6b5c66e0
출처 데이터셋
uspto-grants-2009_02
특허 번호
US07495018B2

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