Trifluoroacetic acid → HCID 178481100, compound

HRID 1624944Notes

Reaction equation

HRID 1624944 reaction equation
FC(F)(F)C(O)=O.C(OC(=O)[NH:14][C:15]1[N:16]=[C:17]([C:21](=[O:38])[NH:22][C:23]2[C:24]([C:28](=[O:37])[NH:29][C:30]3[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=3)=[N:25][NH:26][CH:27]=2)[N:18]([CH3:20])[CH:19]=1)(C)(C)C>ClCCl>[F:36][C:33]1[CH:34]=[CH:35][C:30]([NH:29][C:28]([C:24]2[C:23]([NH:22][C:21]([C:17]3[N:18]([CH3:20])[CH:19]=[C:15]([NH2:14])[N:16]=3)=[O:38])=[CH:27][NH:26][N:25]=2)=[O:37])=[CH:31][CH:32]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178481087HCID 178481087, compound

Product 1

HCID 178481100HCID 178481100, compoundYield 64.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (200 μl) was added to a stirred suspension of {2-[3-(4-fluoro-phenylcarbamoyl)-1H-pyrazol-4-ylcarbamoyl]-1-methyl-1H-imidazol-4-yl}-carbamic acid tert-butyl ester (30 mg) in dichloromethane (5 ml), then stirred at room temperature for 2 hours. The solvent was evaporated then re-evaporated with toluene (2×10 ml). The residue was triturated with diethyl ether and the resultant solid collected by filtration. The solid was washed with diethyl ether then dried under vacuum to give 15 mg of 4-[(4-amino-1-methyl-1H-imidazole-2-carbonyl)-amino]-1H-pyrazole-3-carboxylic acid (4-fluoro-phenyl)-amide as an off-white solid. (LC/MS: [M+H]+ 343.72).

Workup

  1. customThe solvent was evaporated
  2. customthen re-evaporated with toluene (2×10 ml)
  3. customThe residue was triturated with diethyl ether
  4. filtrationthe resultant solid collected by filtration
  5. washThe solid was washed with diethyl ether
  6. customthen dried under vacuum

Sources & evidence

ORD record
ord-71f7f0a632a9408e83c33a06a2420a2d
Source dataset
uspto-grants-2014_07
Patent number
US08779147B2

Reaction notes

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