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

HRID 1411233Notes

Reaction equation

HRID 1411233 reaction equation
[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]

Participants

6

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 71522964HCID 71522964, compound

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-77b9287bf45d438c897539d87ccf1bc1
Source dataset
uspto-grants-2014_12
Patent number
US08921576B2

Reaction notes

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