Trifluoroacetic acid → HCID 66740660, compound

HRID 1627282Notes

Reaction equation

HRID 1627282 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:11]2[N:15]([C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)[C:14]([S:23][CH2:24][C:25]3[C:30]([F:31])=[CH:29][C:28]([NH:32]C(=O)OC(C)(C)C)=[CH:27][C:26]=3[F:40])=[N:13][CH:12]=2)([CH3:10])[CH3:9])=[CH:4][C:3]=1[O:41][CH3:42].C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:11]2[N:15]([C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)[C:14]([S:23][CH2:24][C:25]3[C:26]([F:40])=[CH:27][C:28]([NH2:32])=[CH:29][C:30]=3[F:31])=[N:13][CH:12]=2)([CH3:10])[CH3:9])=[CH:4][C:3]=1[O:41][CH3:42]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66741002tert-butyl 4-((5-(2-(4-chloro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazol-2-ylthio)methyl)-3,5-difluorophenylcarbamate

Product 1

HCID 66740660HCID 66740660, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 4-((5-(2-(4-chloro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazol-2-ylthio)methyl)-3,5-difluorophenylcarbamate (75 g, 0.12 mmol) in DCM (300 mL) was added TFA (300 mL) at 0° C. The reaction mixture was warmed to room temperature, stirred for 2 h and evaporated to give 4-((5-(2-(4-chloro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazol-2-ylthio)methyl)-3,5-difluorobenzenamine as a light-pink foam (62 g, quant). 1H NMR (400 MHz, CDCl3): δ 7.65 (s, 1H), 7.20-7.23 (d, 1H), 6.92-6.96 (t, 2H), 6.41-6.50 (m, 6H), 3.91 (s, 2H), 3.79 (s, 3H), 1.58 (s, 6H).

Workup

  1. customevaporated

Sources & evidence

ORD record
ord-a3c57a5cc1c544a08c92a57d25f59e11
Source dataset
uspto-grants-2014_07
Patent number
US08785488B2

Reaction notes

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