Trifluoroacetic acid → HCID 68570515, compound

HRID 2100511Notes

Reaction equation

HRID 2100511 reaction equation
[F:1][C:2]1[CH:3]=[N:4][C:5]([NH:11]CC2C=CC(OC)=CC=2)=[C:6]([CH:10]=1)[C:7]([NH2:9])=[O:8].C(O)(C(F)(F)F)=O>C(Cl)Cl.C1(OC)C=CC=CC=1>[NH2:11][C:5]1[N:4]=[CH:3][C:2]([F:1])=[CH:10][C:6]=1[C:7]([NH2:9])=[O:8]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68569400HCID 68569400, compound

Product 1

HCID 68570515HCID 68570515, compoundYield 81.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 7519AnisoleSolvent

Procedure

5-Fluoro-2-(4-methoxy-benzylamino)-nicotinamide (220 mg, 0.80 mmol) in CH2Cl2 (2 ml) and anisole (1 ml) was treated with TFA (2.57 ml, 34.6 mmol) at 60° C. for 3 hours. The reaction mixture was brought to dryness and the residue purified by column chromatography (silica gel, EtOAc/heptane, 1/4) to yield 2-amino-5-fluoro-nicotinamide (100 mg, 0.65 mmol; 81%) as yellow solid. MS (m/e): 156.1 [M+H+].

Workup

  1. customthe residue purified by column chromatography (silica gel, EtOAc/heptane, 1/4)

Sources & evidence

ORD record
ord-5fd5853189b740bd8945e01bb80ab5d5
Source dataset
uspto-grants-2009_08
Patent number
US07572801B2

Reaction notes

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