Trifluoroacetic anhydride → HCID 46908652, compound

HRID 1159685Notes

Reaction equation

HRID 1159685 reaction equation
[NH2:1][C:2](=O)[CH2:3][C:4]1[C:5]([Cl:33])=[N:6][C:7]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([NH:20][C:21]([C:23]3[CH:32]=[CH:31][C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[CH:24]=3)=[O:22])=[CH:16][CH:15]=2)=[N:8][C:9]=1[N:10]([CH3:12])[CH3:11].FC(F)(F)C(OC(=O)C(F)(F)F)=O>N1C=CC=CC=1>[Cl:33][C:5]1[C:4]([CH2:3][C:2]#[N:1])=[C:9]([N:10]([CH3:12])[CH3:11])[N:8]=[C:7]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([NH:20][C:21]([C:23]3[CH:32]=[CH:31][C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[CH:24]=3)=[O:22])=[CH:16][CH:15]=2)[N:6]=1

Participants

4

Reactant 2

HCID 9845Trifluoroacetic anhydrideHCID 46908651HCID 46908651, compound

Product 1

HCID 46908652HCID 46908652, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of N-(4-{[5-(2-amino-2-oxoethyl)-4-chloro-6-(dimethylamino)pyrimidin-2-yl]methyl}phenyl)-2-naphthamide (0.360 g, 0.76 mmol) in pyridine (15 mL) at rt was added trifluoroacetic anhydride (0.161 mL, 1.14 mmol) dropwise and the resulting reaction mixture was stirred at room temperature for 15 hours. The volatiles were removed in vacuo and the remaining residue was partitioned between EtOAc and saturated aqueous ammonium chloride solution. The separated organic layer was washed with brine, dried over anhydrous Na2SO4, filtered, and concentrated in vacuo. Purification of the resulting crude product by silica gel chromatography eluting with 20% EtOH in CHCl3 gave N-(4-{[4-chloro-5-(cyanomethyl)-6-(dimethyl-amino)pyrimidin-2-yl]methyl}phenyl)-2-naphthamide as an amorphous solid (0.345 g, 100%).

Workup

  1. customthe resulting reaction mixture
  2. customThe volatiles were removed in vacuo
  3. customthe remaining residue was partitioned between EtOAc and saturated aqueous ammonium chloride solution
  4. washThe separated organic layer was washed with brine
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customPurification of the resulting crude product by silica gel chromatography
  9. washeluting with 20% EtOH in CHCl3

Sources & evidence

ORD record
ord-eac7c54f0dcf4575a741e641d1c49d99
Source dataset
uspto-grants-2010_10
Patent number
US07812160B2

Reaction notes

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