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

HRID 1727375ノート

反応式

HRID 1727375 の反応式
[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]

参加物

6

反応物 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

生成物 1

HCID 57349381Tert-butyl 4-[5-(2-acetamidopyridin-4-yl)-4-(3-chlorophenyl)-1,3-thiazol-2-yl]piperidine-1-carboxylate収率 102.6%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-25502566e52048fabecc89ee6b5c66e0
出典データセット
uspto-grants-2009_02
特許番号
US07495018B2

反応ノート

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