Dimethylformamide → [4-(6-Chloro-benzothiazol-2-yl)-piperazin-1-yl]-(2-morpholin-4-yl-5-nitro-phenyl)-methanone

HRID 1294758Notes

Reaction equation

HRID 1294758 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.CN(C)C=O.C(N(C(C)C)C(C)C)C.[Cl:33][C:34]1[CH:48]=[CH:47][C:37]2[N:38]=[C:39]([N:41]3[CH2:46][CH2:45][NH:44][CH2:43][CH2:42]3)[S:40][C:36]=2[CH:35]=1>>[Cl:33][C:34]1[CH:48]=[CH:47][C:37]2[N:38]=[C:39]([N:41]3[CH2:46][CH2:45][N:44]([C:9]([C:8]4[CH:12]=[C:13]([N+:16]([O-:18])=[O:17])[CH:14]=[CH:15][C:7]=4[N:1]4[CH2:2][CH2:3][O:4][CH2:5][CH2:6]4)=[O:11])[CH2:43][CH2:42]3)[S:40][C:36]=2[CH:35]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 27257552-Morpholino-5-nitrobenzoic acidHCID 27465956-Chloro-2-(piperazin-1-yl)-1,3-benzothiazole

Product 1

HCID 11677524[4-(6-Chloro-benzothiazol-2-yl)-piperazin-1-yl]-(2-morpholin-4-yl-5-nitro-phenyl)-methanone

Procedure

To a solution of 0.25 mmol 2-morpholin-4-yl-5-nitro-benzoic acid (Example 2.1) in 0.7 ml dimethylformamide 0.26 mmol TBTU, 1.6 mmol N-ethyldiisopropylamine and 0.25 mmol 6-chloro-2-piperazin-1-yl-benzothiazole were successively added. The reaction was then stirred at RT for two hours, concentrated in vacuo and treated with 5 ml water. The solid is filtered off and recrystallized form methanol to yield the title compound as a yellow solid.

Workup

  1. concentrationconcentrated in vacuo
  2. additiontreated with 5 ml water
  3. filtrationThe solid is filtered off
  4. customrecrystallized
  5. customform methanol

Sources & evidence

ORD record
ord-5ec4d4a178164c1788c21dd4b9ae3558
Source dataset
uspto-grants-2007_07
Patent number
US07241761B2

Reaction notes

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