Trifluoroacetic acid → HCID 178509949, compound

HRID 1875074Notes

Reaction equation

HRID 1875074 reaction equation
[C:1]([OH:7])([C:3]([F:6])([F:5])[F:4])=[O:2].CC(OC([N:15]([C:23]1[NH:24][C:25]([C:29]([NH:31][CH2:32][C:33]2[CH:38]=[CH:37][C:36]([Cl:39])=[C:35]([O:40][C:41]3[CH:46]=[C:45]([C:47]#[N:48])[CH:44]=[C:43]([Cl:49])[CH:42]=3)[C:34]=2[F:50])=[O:30])=[C:26]([Br:28])[N:27]=1)C(OC(C)(C)C)=O)=O)(C)C>ClCCl>[F:4][C:3]([F:6])([F:5])[C:1]([OH:7])=[O:2].[NH2:15][C:23]1[NH:24][C:25]([C:29]([NH:31][CH2:32][C:33]2[CH:38]=[CH:37][C:36]([Cl:39])=[C:35]([O:40][C:41]3[CH:46]=[C:45]([C:47]#[N:48])[CH:44]=[C:43]([Cl:49])[CH:42]=3)[C:34]=2[F:50])=[O:30])=[C:26]([Br:28])[N:27]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178454340HCID 178454340, compound

Product 1

HCID 178509949HCID 178509949, compoundYield 41.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (3.30 μl, 0.043 mmol) was added to a solution of bis(1,1-dimethylethyl)(4-bromo-5-{[({4-chloro-3-[(3-chloro-5-cyanophenyl)oxy]-2-fluorophenyl}methyl)amino]carbonyl}-1H-imidazol-2-yl)imidodicarbonate (0.030 g, 0.043 mmol) in dichloromethane (2 mL). The mixture was stirred at RT overnight. The solvent was evaporated and the residue was purified by reverse phase HPLC (acetonitrile:water with 0. % TFA) to give the title compound (11 mg, 41%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.02-8.12 (m, 1H), 7.80 (s, 1H), 7.46-7.53 (m, 2H), 7.44 (s, 1H), 7.35 (t, 1H), 6.61 (br. s., 2H), 4.47 (s, 2H). ES MS m/z 499.

Workup

  1. customThe solvent was evaporated
  2. customthe residue was purified by reverse phase HPLC (acetonitrile:water with 0. % TFA)

Sources & evidence

ORD record
ord-486d3901301e4e20868065d48afe4d17
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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