2-Morpholino-5-nitrobenzoic acid → (2-Morpholin-4-yl-5-nitro-phenyl)-[4-(5-trifluoromethyl-[1,3,4]thiadiazol-2-yl)-piperazin-1-yl]-methanone

HRID 1352404Notes

Reaction equation

HRID 1352404 reaction equation
[N:1]1([C:7]2[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][C:8]=2[C:9]([OH:11])=O)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.FC(F)(F)C(O)=O.[F:26][C:27]([F:40])([F:39])[C:28]1[S:32][C:31]([N:33]2[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]2)=[N:30][N:29]=1>>[N:1]1([C:7]2[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][C:8]=2[C:9]([N:36]2[CH2:35][CH2:34][N:33]([C:31]3[S:32][C:28]([C:27]([F:39])([F:26])[F:40])=[N:29][N:30]=3)[CH2:38][CH2:37]2)=[O:11])[CH2:2][CH2:3][O:4][CH2:5][CH2:6]1

Participants

3

Reactant 2

HCID 27257552-Morpholino-5-nitrobenzoic acidHCID 211001991-(5-Trifluoromethyl-[1,3,4]thiadiazol-2-yl)-piperazine trifluoroacetate

Product 1

HCID 21100256(2-Morpholin-4-yl-5-nitro-phenyl)-[4-(5-trifluoromethyl-[1,3,4]thiadiazol-2-yl)-piperazin-1-yl]-methanoneYield 34%

Procedure

Prepared in analogy to example 1 (b) from 2-morpholin-4-yl-5-nitro-benzoic acid (Example A27) and 1-(5-trifluoromethyl-[1,3,4]thiadiazol-2-yl)-piperazine trifluoroacetate (Example 62(b)). The crude material was purified by chromatography (SiO2, methanol/dichloromethane) to yield the title compound as a brown solid (yield 34%). MS (m/e): 473.4 (M+H+, 100%).

Workup

  1. customThe crude material was purified by chromatography (SiO2, methanol/dichloromethane)

Sources & evidence

ORD record
ord-2b6a564cd6cb48d1950e2f61efee3666
Source dataset
uspto-grants-2007_05
Patent number
US07220744B2

Reaction notes

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