Trifluoroacetic acid → HCID 66739983, compound

HRID 1627268Notes

Reaction equation

HRID 1627268 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:35]C(=O)OC(C)(C)C)[CH:5]=[C:6]([F:34])[C:7]=1[CH2:8][S:9][C:10]1[N:11]([C:27]2[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=2)[C:12]([C:15]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[C:20]([O:25][CH3:26])[CH:19]=2)([CH3:17])[CH3:16])=[CH:13][N:14]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]=[C:6]([F:34])[C:7]=1[CH2:8][S:9][C:10]1[N:11]([C:27]2[CH:28]=[CH:29][C:30]([F:33])=[CH:31][CH:32]=2)[C:12]([C:15]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[C:20]([O:25][CH3:26])[CH:19]=2)([CH3:16])[CH3:17])=[CH:13][N:14]=1)[NH2:35]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66741137tert-butyl 3-chloro-4-((5-(2-(4-chloro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazol-2-ylthio)methyl)-5-fluorophenylcarbamate

Product 1

HCID 66739983HCID 66739983, compoundYield 90.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl 3-chloro-4-((5-(2-(4-chloro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazol-2-ylthio)methyl)-5-fluorophenylcarbamate (200 mg) in DCM (1 mL) was treated with TFA (1 mL) with stirring. After 1 h, the solution was concentrated under reduced pressure, diluted with DCE (5 mL). The organic layer was washed with water, satd NaHCO3 and brine, then dried (MgSO4) and concentrated to afford the title compound (152 mg, 90%). 1H NMR (400 MHz, MeOD) δ 7.40 (s, 1H), 7.36 (d, J=9.1 Hz, 1H), 6.93 (d, J=8.4, 1H), 6.87 (d, J=8.4 Hz, 1H), 6.68-6.61 (m, 2H), 6.53 (s, 1H), 6.40-6.27 (m, 3H), 4.01 (s, 2H), 3.76 (s, 3H), 1.58 (s, 6H); MS (EI) m/z 534 (MH+).

Workup

  1. concentrationthe solution was concentrated under reduced pressure
  2. additiondiluted with DCE (5 mL)
  3. washThe organic layer was washed with water
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-e501e54871ea4d779394bc6ebf33f480
Source dataset
uspto-grants-2014_07
Patent number
US08785488B2

Reaction notes

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