HCID 178433035, compound → (RS)-1-{2-[4-(4-Fluorophenyl)-1H-imidazol-2-ylmethyl]-piperazin-1-yl}-1-[5-(4-fluorophenyl)-2-methylthiazol-4-yl]-methanone

HRID 549357Notes

Reaction equation

HRID 549357 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]([C:16]2[N:17]=[C:18]([CH3:28])[S:19][C:20]=2[C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=2)=[O:15])[CH:10]([CH2:29][C:30]2[NH:31][CH:32]=[C:33]([C:35]3[CH:40]=[CH:39][C:38]([F:41])=[CH:37][CH:36]=3)[N:34]=2)[CH2:9]1)=O)(C)(C)C>C(O)(C(F)(F)F)=O>[F:41][C:38]1[CH:39]=[CH:40][C:35]([C:33]2[N:34]=[C:30]([CH2:29][CH:10]3[CH2:9][NH:8][CH2:13][CH2:12][N:11]3[C:14]([C:16]3[N:17]=[C:18]([CH3:28])[S:19][C:20]=3[C:21]3[CH:22]=[CH:23][C:24]([F:27])=[CH:25][CH:26]=3)=[O:15])[NH:31][CH:32]=2)=[CH:36][CH:37]=1

Participants

3

Reactant 1

HCID 178433035HCID 178433035, compound

Product 1

HCID 178433009(RS)-1-{2-[4-(4-Fluorophenyl)-1H-imidazol-2-ylmethyl]-piperazin-1-yl}-1-[5-(4-fluorophenyl)-2-methylthiazol-4-yl]-methanone

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

3-[4-(4-Fluorophenyl)-1H-imidazol-2-ylmethyl]-4-{1-[5-(4-fluorophenyl)-2-methylthiazol-4-yl]-methanoyl}-piperazine-1-carboxylic acid tert-butyl ester description 112 (0.130 g) was dissolved in TFA and stirred under argon at room temperature for 3 hours. The TFA was evaporated and the residue chromatographed over silica gel, eluting with a gradient of 0 to 10% [9:1 methanol/conc. ammonia solution] in dichloromethane. The title compound was obtained as a white foam (0.095 g), mass spectrum (API+) 480 [MH+], C25H23F2N5OS requires 479.

Workup

  1. customThe TFA was evaporated
  2. customthe residue chromatographed over silica gel
  3. washeluting with a gradient of 0 to 10% [9:1 methanol/conc. ammonia solution] in dichloromethane

Sources & evidence

ORD record
ord-9d5c058ebb5f4fa28a4fa11fa2e4544d
Source dataset
uspto-grants-2011_05
Patent number
US07943645B2

Reaction notes

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