Trifluoroacetic acid → 5-(4-(aminomethyl)-2-fluorophenyl)-1-methylpyridin-2(1H)-one

HRID 711232Notes

Reaction equation

HRID 711232 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][C:16]=1[C:17]1[CH:22]=[CH:21][C:20](=[O:23])[N:19]([CH3:24])[CH:18]=1)[CH2:5][NH:6]C(=O)OC(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[NH2:6][CH2:5][C:4]1[CH:14]=[CH:15][C:16]([C:17]2[CH:22]=[CH:21][C:20](=[O:23])[N:19]([CH3:24])[CH:18]=2)=[C:2]([F:1])[CH:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86679718Tert-butyl 3-fluoro-4-(1-methyl-6-oxo-1,6-dihydropyridin-3-yl)benzylcarbamate

Product 1

HCID 672086765-(4-(aminomethyl)-2-fluorophenyl)-1-methylpyridin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The crude tert-butyl 3-fluoro-4-(1-methyl-6-oxo-1,6-dihydropyridin-3-yl)benzylcarbamate 21-6 (10 mg, obtained in Step 3) was stirred with trifluoroacetic acid (TFA, 0.3 mL) in dichloromethane (1 mL) overnight. Evaporation under reduced pressure (with the addition of some toluene to aid evaporation of the residual TFA) followed by lyophilization gave the crude 5-(4-(aminomethyl)-2-fluorophenyl)-1-methylpyridin-2(1H)-one 21-7.

Workup

  1. customEvaporation under reduced pressure (
  2. additionwith the addition of some toluene
  3. customevaporation of the residual TFA)

Sources & evidence

ORD record
ord-f90229edfe514a64af7e94195d3d9fc5
Source dataset
uspto-grants-2015_11
Patent number
US09181235B2

Reaction notes

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