Trifluoroacetic acid → HCID 178510248, compound

HRID 1875183Notes

Reaction equation

HRID 1875183 reaction equation
CC(OC([N:8]([C:16]1[NH:17][C:18]([C:22]([NH:24][CH2:25][C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[C:28]([O:33][C:34]3[CH:39]=[C:38]([CH:40]4[CH2:42][CH2:41]4)[CH:37]=[C:36]([C:43]#[N:44])[CH:35]=3)[C:27]=2[F:45])=[O:23])=[C:19]([Cl:21])[N:20]=1)C(OC(C)(C)C)=O)=O)(C)C.[C:46]([OH:52])([C:48]([F:51])([F:50])[F:49])=[O:47]>C(Cl)Cl>[F:49][C:48]([F:51])([F:50])[C:46]([OH:52])=[O:47].[NH2:8][C:16]1[NH:17][C:18]([C:22]([NH:24][CH2:25][C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[C:28]([O:33][C:34]3[CH:39]=[C:38]([CH:40]4[CH2:42][CH2:41]4)[CH:37]=[C:36]([C:43]#[N:44])[CH:35]=3)[C:27]=2[F:45])=[O:23])=[C:19]([Cl:21])[N:20]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178454346HCID 178454346, compound

Product 1

HCID 178510248HCID 178510248, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of bis(1,1-dimethylethyl)(4-chloro-5-{[({4-chloro-3-[(3-cyano-5-cyclopropylphenyl)oxy]-2-fluorophenyl}methyl)amino]carbonyl}-1H-imidazol-2-yl)imidodicarbonate (161 mg, 0.244 mmol) in DCM (5 ml) was added TFA (2.5 ml) and the reaction mixture was stirred at RT for 3 hours. The solvent was removed and the crude material was purified via reverse phase HPLC to give 2-amino-4-chloro-N-({4-chloro-3-[(3-cyano-5-cyclopropylphenyl)oxy]-2-fluorophenyl}methyl)-1H-imidazole-5-carboxamide trifluoroacetate (59 mg, 0.103 mmol, 42% yield).

Workup

  1. customThe solvent was removed
  2. customthe crude material was purified via reverse phase HPLC

Sources & evidence

ORD record
ord-f221eee8757244f6b8bf1a26085654d7
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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