Diisopropylethylamine → (RS)-4-{1-[5-(4-Fluorophenyl)-2-methylthiazol-4-yl]-methanoyl}-3-[2-(4-fluoro-phenyl)-2-oxo-ethoxycarbonylmethyl]-piperazine-1-carboxylic acid tert-butyl ester

HRID 30188Notes

Reaction equation

HRID 30188 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][NH:11][CH:10]([CH2:14][C:15]([O:17][CH2:18][C:19]([C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=2)=[O:20])=[O:16])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C.[F:61][C:62]1[CH:67]=[CH:66][C:65]([C:68]2[S:72][C:71]([CH3:73])=[N:70][C:69]=2[C:74](O)=[O:75])=[CH:64][CH:63]=1>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:74]([C:69]2[N:70]=[C:71]([CH3:73])[S:72][C:68]=2[C:65]2[CH:66]=[CH:67][C:62]([F:61])=[CH:63][CH:64]=2)=[O:75])[CH:10]([CH2:14][C:15]([O:17][CH2:18][C:19]([C:21]2[CH:22]=[CH:23][C:24]([F:27])=[CH:25][CH:26]=2)=[O:20])=[O:16])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 223241255-(4-Fluorophenyl)-2-methyl-1,3-thiazole-4-carboxylic acidHCID 67158269(RS)-3-[2-(4-Fluorophenyl)-2-oxo-ethoxycarbonylmethyl]piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 67158091(RS)-4-{1-[5-(4-Fluorophenyl)-2-methylthiazol-4-yl]-methanoyl}-3-[2-(4-fluoro-phenyl)-2-oxo-ethoxycarbonylmethyl]-piperazine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(RS)-3-[2-(4-Fluorophenyl)-2-oxo-ethoxycarbonylmethyl]-piperazine-1-carboxylic acid tert-butyl ester description 110 (0.887 g) was reacted with HATU (0.932 g), diisopropylethylamine (1.30 ml) and 5-(4-fluoro-phenyl)-2-methyl-thiazole-4-carboxylic acid (0.707 g) in dry DMF (8 ml) according to the method of description 20. Silica gel column chromatography, eluting with ethyl acetate-hexane mixtures provided the title compound as a white foam (1.168 g), mass spectrum (API+) 600 [MH+], C30H31F2N3O6S requires 599.

Workup

  1. washSilica gel column chromatography, eluting with ethyl acetate-hexane mixtures

Sources & evidence

ORD record
ord-4810da5bcbf1440bb9892937829dc6c4
Source dataset
uspto-grants-2008_09
Patent number
US07423052B2

Reaction notes

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