Acetyl chloride → 1'-acetyl-5-bromo-N-(5-chlorothiazol-2-yl)spiro[indoline-3,3'-pyrrolidine]-1-carboxamide

HRID 1411233ノート

反応式

HRID 1411233 の反応式
[Br:1][C:2]1[CH:3]=[C:4]2[C:10]3([CH2:14][CH2:13][NH:12][CH2:11]3)[CH2:9][N:8]([C:15]([NH:17][C:18]3[S:19][C:20]([Cl:23])=[CH:21][N:22]=3)=[O:16])[C:5]2=[CH:6][CH:7]=1.C(N(CC)CC)C.[C:31](Cl)(=[O:33])[CH3:32]>C(Cl)Cl.O>[C:31]([N:12]1[CH2:13][CH2:14][C:10]2([C:4]3[C:5](=[CH:6][CH:7]=[C:2]([Br:1])[CH:3]=3)[N:8]([C:15]([NH:17][C:18]3[S:19][C:20]([Cl:23])=[CH:21][N:22]=3)=[O:16])[CH2:9]2)[CH2:11]1)(=[O:33])[CH3:32]

参加物

6

反応物 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 71522964HCID 71522964、化合物

生成物 1

HCID 715229651'-acetyl-5-bromo-N-(5-chlorothiazol-2-yl)spiro[indoline-3,3'-pyrrolidine]-1-carboxamide収率 94%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

The 5-bromo-N-(5-chlorothiazol-2-yl)spiro[indoline-3,3′-pyrrolidine]-1-carboxamide (48.2 mg, 0.105 mmol) obtained in Example 2 was dissolved in methylene chloride (1.0 mL). Thereafter, triethylamine (34.4 μL, 0.315 mmol) and acetyl chloride (7.5 μL, 0.105 mmol) were added to the above obtained solution under cooling on ice, and the obtained mixture was then stirred for 1 hour. The reaction solution was diluted with water, and was then extracted with methylene chloride. The organic layer was washed with brine, and was then dried over anhydrous sodium sulfate, followed by concentration in vacuo. The obtained residue was purified by silica gel column chromatography (chloroform:methanol=10:1) to obtain the captioned compound (45.0 mg, 94%) in the form of a white solid.

後処理

  1. temperatureunder cooling on ice
  2. extractionwas then extracted with methylene chloride
  3. washThe organic layer was washed with brine
  4. dry with materialwas then dried over anhydrous sodium sulfate
  5. concentrationfollowed by concentration in vacuo
  6. customThe obtained residue was purified by silica gel column chromatography (chloroform:methanol=10:1)

出典と根拠

ORDレコード
ord-77b9287bf45d438c897539d87ccf1bc1
出典データセット
uspto-grants-2014_12
特許番号
US08921576B2

反応ノート

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