Trifluoroacetic acid → HCID 178510244, compound

HRID 1875203Notes

Reaction equation

HRID 1875203 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([C:9]#[N:10])=[CH:4][C:3]=1[O:11][C:12]1[C:13]([F:37])=[C:14]([CH2:19][NH:20][C:21]([C:23]2[N:27](COCC[Si](C)(C)C)[CH:26]=[N:25][C:24]=2[Cl:36])=[O:22])[CH:15]=[CH:16][C:17]=1[Cl:18].C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([C:9]#[N:10])=[CH:4][C:3]=1[O:11][C:12]1[C:13]([F:37])=[C:14]([CH2:19][NH:20][C:21]([C:23]2[NH:27][CH:26]=[N:25][C:24]=2[Cl:36])=[O:22])[CH:15]=[CH:16][C:17]=1[Cl:18]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68722215HCID 68722215, compound

Product 1

HCID 178510244HCID 178510244, compoundYield 33.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-({3-[(2-amino-5-cyano-4-fluorophenyl)oxy]-4-chloro-2-fluorophenyl}methyl)-4-chloro-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-imidazole-5-carboxamide (35 mg, 0.062 mmol) in DCM (6 ml) was added TFA (3.0 mL) and the reaction mixture was stirred for 3 hours at RT. The solvent was removed and the crude material was purified via reverse phase HPLC and neutralized to give N-({3-[(2-amino-5-cyano-4-fluorophenyl)oxy]-4-chloro-2-fluorophenyl}methyl)-4-chloro-1H-imidazole-5-carboxamide (9.0 mg, 0.021 mmol, 33% yield). 1H NMR (400 MHz, METHANOL-d4) δ ppm 7.70 (s, 1H), 7.20-7.42 (m, 2H), 6.58 (d, 1H), 6.49 (d, 1H), 4.62 (s, 2H). LC-MS (ES+) m/z 438.13, [M+H].

Workup

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

Sources & evidence

ORD record
ord-965c097707454f9a9826d35b80cc47ee
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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