(RS)-4-{1-[5-(4-Fluorophenyl)-2-methylthiazol-4-yl]-methanoyl}-3-[4-(4-fluoro-phenyl)-oxazol-2-ylmethyl]-piperazine-1-carboxylic acid tert-butyl ester → 1-[5-(4-Fluorophenyl)-2-methyl-thiazol-4-yl]1-{2-[4-(4-fluorophenyl)-oxazol-2-ylmethyl]-piperazin-1-yl}-methanone

HRID 549358Notes

Reaction equation

HRID 549358 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[O: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>FC(F)(F)C(O)=O>[F:27][C:24]1[CH:25]=[CH:26][C:21]([C:20]2[S:19][C:18]([CH3:28])=[N:17][C:16]=2[C:14]([N:11]2[CH2:12][CH2:13][NH:8][CH2:9][CH:10]2[CH2:29][C:30]2[O:31][CH:32]=[C:33]([C:35]3[CH:36]=[CH:37][C:38]([F:41])=[CH:39][CH:40]=3)[N:34]=2)=[O:15])=[CH:22][CH:23]=1

Participants

3

Reactant 1

HCID 67157954(RS)-4-{1-[5-(4-Fluorophenyl)-2-methylthiazol-4-yl]-methanoyl}-3-[4-(4-fluoro-phenyl)-oxazol-2-ylmethyl]-piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 671579551-[5-(4-Fluorophenyl)-2-methyl-thiazol-4-yl]1-{2-[4-(4-fluorophenyl)-oxazol-2-ylmethyl]-piperazin-1-yl}-methanoneYield 12.1%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

4-{1-[5-(4-Fluorophenyl)-2-methyl-thiazol-4-yl]-methanoyl}-3-[4-(4-fluoro-phenyl)-oxazol-2-ylmethyl]-piperazine-1-carboxylic acid tert-butyl ester (0.130 g) was dissolved in trifluoroacetic acid (10 ml) and stirred at room temperature for 2 hours. The reaction mixture was then evaporated to dryness at reduced pressure and the residue was chromatographed over silica gel. Elution with a gradient of 0 to 10% [9:1 methanol/conc. ammonia solution] in dichloromethane provided the title compound as a pale yellow gum (0.013 g), mass spectrum (API+) 481 [MH+], C25H22F2N4O2S requires 480.

Workup

  1. customThe reaction mixture was then evaporated to dryness at reduced pressure
  2. customthe residue was chromatographed over silica gel
  3. washElution with a gradient of 0 to 10% [9:1 methanol/conc. ammonia solution] in dichloromethane

Sources & evidence

ORD record
ord-d6c380d0d5f649d98525d3c3774f0ec9
Source dataset
uspto-grants-2011_05
Patent number
US07943645B2

Reaction notes

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