Sodium Bicarbonate → 1-[4-[4-[(5R)-4,5-dihydro-5-phenyl-3-isoxazolyl]-2-thiazolyl]-1-piperidinyl]-N-[2,5-dimethylphenyl]carboxamide

HRID 2096031ノート

反応式

HRID 2096031 の反応式
CC1C=CC(C)=CC=1[NH:9][C:10]([N:12]1[CH2:17][CH2:16][CH:15]([C:18](=[S:20])[NH2:19])[CH2:14][CH2:13]1)=O.Br[CH2:22][C:23]([C:25]1[CH2:29][C@H:28]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[O:27][N:26]=1)=O.[C:36](=[O:39])(O)[O-].[Na+]>CC(C)=O>[C:30]1([C@@H:28]2[O:27][N:26]=[C:25]([C:23]3[N:19]=[C:18]([CH:15]4[CH2:14][CH2:13][N:12]([C:10]5([NH:9][CH:36]=[O:39])[CH:31]=[C:30]([CH3:35])[CH:28]=[CH:29][CH:25]5[CH3:23])[CH2:17][CH2:16]4)[S:20][CH:22]=3)[CH2:29]2)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

参加物

5

反応物 3

HCID 516892Sodium BicarbonateHCID 866312472-bromo-1-[(5R)-4,5-dihydro-5-phenyl-3-isoxazolyl]ethanoneHCID 86645615N-(2,5-dimethylphenyl)-4-thiocarbamoylpiperidine-carboxamide2 回

生成物 1

HCID 1317305961-[4-[4-[(5R)-4,5-dihydro-5-phenyl-3-isoxazolyl]-2-thiazolyl]-1-piperidinyl]-N-[2,5-dimethylphenyl]carboxamide

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

反応条件

温度
45 °C

実験手順

A mixture of N-(2,5-dimethylphenyl)-4-thiocarbamoylpiperidine carboxamide (i.e. the product of Example 14, Step B) (291 mg, 1.0 mmol) and 409 (i.e. the product of Example 12, Step E) (268 mg, 1.0 mmol) in acetone (10 mL) was vortexed for 16 h and then heated at 45° C. for 1 h. The reaction mixture was allowed to cool to room temperature, treated with solid sodium bicarbonate (168 mg, 2.0 mmol), and stirred for 1 h. The reaction mixture was then concentrated under reduced pressure, diluted with ethyl acetate, washed with water and brine, dried (MgSO4), and concentrated under reduced pressure to give the title product as a pale-yellow foam. The sample was dissolved in methyl acetate (2 mL) and allowed to sit at room temperature and then at 0° C. to give 220 mg of colorless crystals melting at 120-125° C. A second preparation was crystallized from methanol to give large prisms melting at 121-124° C.

後処理

  1. temperatureto cool to room temperature
  2. concentrationThe reaction mixture was then concentrated under reduced pressure
  3. additiondiluted with ethyl acetate
  4. washwashed with water and brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-0679f54b3ef04b44b9ff53f8b0578d78
出典データセット
uspto-grants-2013_05
特許番号
US08449898B2

反応ノート

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