Trifluoroacetic anhydride → HCID 71251272, compound

HRID 1055127Notes

Reaction equation

HRID 1055127 reaction equation
[F:1][C:2]1[C:3]([NH:18][CH:19]([C:24]([CH3:27])([CH3:26])[CH3:25])[CH2:20][C:21]([NH2:23])=O)=[N:4][C:5]([C:8]2[C:16]3[C:11](=[N:12][CH:13]=[C:14]([F:17])[CH:15]=3)[NH:10][CH:9]=2)=[N:6][CH:7]=1.FC(F)(F)C(OC(=O)C(F)(F)F)=O>N1C=CC=CC=1>[F:1][C:2]1[C:3]([NH:18][CH:19]([C:24]([CH3:27])([CH3:26])[CH3:25])[CH2:20][C:21]#[N:23])=[N:4][C:5]([C:8]2[C:16]3[C:11](=[N:12][CH:13]=[C:14]([F:17])[CH:15]=3)[NH:10][CH:9]=2)=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 9845Trifluoroacetic anhydrideHCID 71251276HCID 71251276, compound2×

Product 1

HCID 71251272HCID 71251272, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of racemic 3-(5-fluoro-2-(5-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-4-ylamino)-4,4-dimethylpentanamide, 164a, (0.250 g, 0.668 mmol) in pyridine was cooled to 0° C. and treated with trifluoroacetic acid anhydride (0.278 mL, 2.003 mmol). After 2 hours at 0° C., the reaction was concentrated to dryness and the residue was purified by silica gel chromatography (EtOAc) to afford 150 mg of desired product: LCMS Gradient 10-90%, 0.1% formic acid, 5 minutes, C18/ACN, Retention Time=2.41 minutes (M+H) 357.47.

Workup

  1. concentrationthe reaction was concentrated to dryness
  2. customthe residue was purified by silica gel chromatography (EtOAc)

Sources & evidence

ORD record
ord-6e77126b5ddd43b0a09699bbc5c914db
Source dataset
uspto-grants-2016_07
Patent number
US09394302B2

Reaction notes

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