Trifluoroacetic acid → HCID 178474456, compound

HRID 1875238Notes

Reaction equation

HRID 1875238 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([N:37](C(=O)C)[C:38](=[O:40])[CH3:39])[N:5](COCC[Si](C)(C)C)[C:6]=1[C:7]([NH:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([O:18][C:19]2[CH:24]=[C:23]([C:25]#[N:26])[CH:22]=[C:21]([Cl:27])[CH:20]=2)[C:12]=1[F:28])=[O:8].C(O)(C(F)(F)F)=O>C(Cl)Cl>[C:38]([NH:37][C:4]1[NH:5][C:6]([C:7]([NH:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([O:18][C:19]3[CH:24]=[C:23]([C:25]#[N:26])[CH:22]=[C:21]([Cl:27])[CH:20]=3)[C:12]=2[F:28])=[O:8])=[C:2]([Cl:1])[N:3]=1)(=[O:40])[CH3:39]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 70937253HCID 70937253, compound

Product 1

HCID 178474456HCID 178474456, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-chloro-N-({4-chloro-3-[(3-chloro-5-cyanophenyl)oxy]-2-fluorophenyl}methyl)-2-(diacetylamino)-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-imidazole-5-carboxamide (0.047 g, 0.071 mmol) and TFA (0.5 mL, 6.5 mmol) in CH2Cl2 (1.0 mL) was stirred at RT overnight. The solution was concentrated and purified by Reverse-Phase HPLC (water:acetonitrile with 0.1% TFA) to provide the title compound (0.007 g, 21%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 11.88 (br. s., 1H) 11.52 (br. s., 1H) 8.81 (br. s., 1H) 7.82 (s, 1H) 7.51-7.55 (m, 2H) 7.50 (s, 1H) 7.47

Workup

  1. concentrationThe solution was concentrated
  2. custompurified by Reverse-Phase HPLC (water:acetonitrile with 0.1% TFA)

Sources & evidence

ORD record
ord-733ce0ecc099486fb88a74fe34d4668d
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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