Acetyl chloride → Ammonia

HRID 1276148ノート

反応式

HRID 1276148 の反応式
[C:1](Cl)(=[O:3])[CH3:2].[O:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[N:7]=[C:6]1[N:14]1[CH2:19][CH2:18][CH2:17][CH2:16][C@H:15]1[C:20]([NH:22][CH2:23][CH2:24][N:25]1[C@H:30]([CH3:31])[CH2:29][NH:28][CH2:27][C@@H:26]1[CH3:32])=[O:21].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[NH3:7].[C:1]([N:28]1[CH2:27][C@@H:26]([CH3:32])[N:25]([CH2:24][CH2:23][NH:22][C:20]([C@@H:15]2[CH2:16][CH2:17][CH2:18][CH2:19][N:14]2[C:6]2[O:5][C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=3[N:7]=2)=[O:21])[C@@H:30]([CH3:31])[CH2:29]1)(=[O:3])[CH3:2]

参加物

6

反応物 3

HCID 6367Acetyl chlorideHCID 11430Potassium CarbonateHCID 9821522(2S)-1-(1,3-benzoxazol-2-yl)-N2-2-[(cis)-2,6-dimethyl-1-piperazinyl]ethyl-2-piperidinecarboxamide

生成物 2

HCID 222AmmoniaHCID 9954262(2S)-N2-2-[(cis)-4-acetyl-2,6-dimethyl-1-piperazinyl]ethyl-1-(1,3-benzoxazol-2-yl)-2-piperidinecarboxamide

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

Acetyl chloride (0.018 ml) was added to a solution of (2S)-1-(1,3-benzoxazol-2-yl)-N2 -2-[(cis)-2,6-dimethyl-1-piperazinyl]ethyl-2-piperidinecarboxamide (0.1 g) [See Example 8] and potassium carbonate (36 mg) in acetonitrile (2 ml). The reaction mixture was stirred at room temperature for 2 hours, after which time the solvent was removed under reduced pressure and the residue partitioned between ethyl acetate and water. The organic layer was separated, dried over magnesium sulphate and the solvent removed under reduced pressure. The crude product was purified by column chromatography on silica gel eluting with a solvent gradient of 97:3.5:0.5 changing to 97:3:1, by volume, dichloromethane: methanol: 0.88 aqueous ammonia solution (93:7:1), to afford (2S)-N2 -2-[(cis)-4-acetyl-2,6-dimethyl-1-piperazinyl]ethyl-1-(1,3-benzoxazol-2-yl)-2-piperidinecarboxamide (91.6 mg) as a white foam.

後処理

  1. customafter which time the solvent was removed under reduced pressure
  2. customthe residue partitioned between ethyl acetate and water
  3. customThe organic layer was separated
  4. dry with materialdried over magnesium sulphate
  5. customthe solvent removed under reduced pressure
  6. customThe crude product was purified by column chromatography on silica gel eluting with a solvent gradient of 97:3.5:0.5 changing to 97:3:1, by volume, dichloromethane

出典と根拠

ORDレコード
ord-08a4c1ee0e7f406180be9d56c4ed6fc5
出典データセット
uspto-grants-2000_12
特許番号
US06166011

反応ノート

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