3-(Trifluoromethyl)benzoyl chloride → HCID 59833927, compound

HRID 252195Notes

Reaction equation

HRID 252195 reaction equation
[NH2:1][C:2]1[C:3]([Cl:22])=[C:4]([C:9]2[C:20]([NH2:21])=[N:19][C:12]3[N:13]=[C:14]([S:17][CH3:18])[N:15]=[CH:16][C:11]=3[CH:10]=2)[C:5]([Cl:8])=[CH:6][CH:7]=1.[F:23][C:24]([F:35])([F:34])[C:25]1[CH:26]=[C:27]([CH:31]=[CH:32][CH:33]=1)[C:28](Cl)=[O:29]>ClCCl>[NH2:21][C:20]1[C:9]([C:4]2[C:3]([Cl:22])=[C:2]([NH:1][C:28](=[O:29])[C:27]3[CH:31]=[CH:32][CH:33]=[C:25]([C:24]([F:23])([F:34])[F:35])[CH:26]=3)[CH:7]=[CH:6][C:5]=2[Cl:8])=[CH:10][C:11]2[CH:16]=[N:15][C:14]([S:17][CH3:18])=[N:13][C:12]=2[N:19]=1

Participants

4

Reactant 2

HCID 752573-(Trifluoromethyl)benzoyl chlorideHCID 59860298Pyrido[2,3-d]pyrimidin-7-amine,6-(3-amino-2,6-dichlorophenyl)-2-(methylthio)-

Product 1

HCID 59833927HCID 59833927, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-(3-amino-2,6-dichloro-phenyl)-2-methylsulfanyl-pyrido[2,3-d]pyrimidin-7-ylamine (600 mg, 1.7 mmol) in dichloromethane (60 ml) is added 3-trifluoromethyl-benzoyl chloride (1.76 g, 8.5 mmol) slowly at 0° C. on an ice bath. The reaction is then raised to room temperature and stirred at room temperature for 18 hours. The reaction mixture is washed with 10% NaHCO3 and brine. The organic phase is dried over MgSO4. The crude product is purified by flash silica gel column eluting with CH2Cl2/MeOH (7N NH3) (v/v: 98/2) to give the title compound as light yellow solid.

Workup

  1. washThe reaction mixture is washed with 10% NaHCO3 and brine
  2. dry with materialThe organic phase is dried over MgSO4
  3. customThe crude product is purified by flash silica gel column
  4. washeluting with CH2Cl2/MeOH (7N NH3) (v/v: 98/2)

Sources & evidence

ORD record
ord-1c9ba7e5f2ae48f0b922e7ad5c0e7c69
Source dataset
uspto-grants-2011_01
Patent number
US07868018B2

Reaction notes

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