3,4-Difluorobenzylamine → 3-Amino-N-(3,4-difluorobenzyl)-4-fluorobenzamide

HRID 335322Notes

Reaction equation

HRID 335322 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[F:12])[C:5]([O:7]C)=O.[F:13][C:14]1[CH:15]=[C:16]([CH2:21][NH2:22])[CH:17]=[CH:18][C:19]=1[F:20]>C1COCC1>[NH2:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[F:12])[C:5]([NH:22][CH2:21][C:16]1[CH:17]=[CH:18][C:19]([F:20])=[C:14]([F:13])[CH:15]=1)=[O:7]

Participants

4

Reactant 2

HCID 1235723,4-DifluorobenzylamineHCID 12541234Methyl 3-amino-4-fluorobenzoate

Product 1

HCID 615200303-Amino-N-(3,4-difluorobenzyl)-4-fluorobenzamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture comprising methyl 3-amino-4-fluorobenzoate (2 g, 11.82 mmol), (3,4-difluorophenyl)methanamine (2.54 g, 17.74 mmol) and TBD (1.646 g, 11.82 mmol) in THF (39.4 ml) was heated at 80° C. overnight. After cooling to RT, the mixture was purified by chromatography on silica eluting with 0-20% 2M NH3 in MeOH/DCM to afford the title compound.

Workup

  1. customthe mixture was purified by chromatography on silica eluting with 0-20% 2M NH3 in MeOH/DCM

Sources & evidence

ORD record
ord-82174f4569c947cca8a41c5f380acdc9
Source dataset
uspto-grants-2014_11
Patent number
US08883819B2

Reaction notes

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