Acetyl chloride → HCID 24760588, compound

HRID 1928360Notes

Reaction equation

HRID 1928360 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]([C:14]3[CH:15]=[C:16]([NH2:20])[CH:17]=[CH:18][CH:19]=3)[N:9]=2)[CH:5]=[C:4]([C:21]2[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][CH:22]=2)[CH:3]=1.[C:31](Cl)(=[O:33])[CH3:32]>CCOC(C)=O.C([O-])(O)=O.[Na+]>[CH3:1][C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]([C:14]3[CH:15]=[C:16]([NH:20][C:31](=[O:33])[CH3:32])[CH:17]=[CH:18][CH:19]=3)[N:9]=2)[CH:5]=[C:4]([C:21]2[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:28])[F:29])=[CH:23][CH:22]=2)[CH:3]=1

Participants

5

Reactant 2

HCID 6367Acetyl chlorideHCID 24760586HCID 24760586, compound

Product 1

HCID 24760588HCID 24760588, compoundYield 60.4%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

To a stirred and cooled solution of 3-{4-[6-methyl-4-(4-trifluoromethyl-phenyl)-pyridin-2-yl]-pyrimidin-2-yl}-phenylamine (example 326) (0.150 g, 0.369 mmol) in EtOAc (2 mL) and sat. NaHCO3-sol. (1 mL) was added acetyl chloride (0.030 mL, 0.406 mmol) and the mixture was stirred at 23° C. for 1 h. Diluted with EtOAc, washed with sat. NaHCO3-sol. and water, dried the organic layer over Na2SO4. Removal of the solvent in vacuum left a crude product which was purified by trituration with diethyl ether to give the title compound as a white solid (0.100 g, 60%). MS (ISP) 449.3 [(M+H)+].

Workup

  1. stirringthe mixture was stirred at 23° C. for 1 h
  2. washwashed with sat. NaHCO3-sol
  3. dry with materialand water, dried the organic layer over Na2SO4
  4. customRemoval of the solvent in vacuum
  5. waitleft a crude product which
  6. customwas purified by trituration with diethyl ether

Sources & evidence

ORD record
ord-be78177525344795aa4a88d9591aaf19
Source dataset
uspto-grants-2012_05
Patent number
US08183262B2

Reaction notes

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