Water → 5-(3-(4-(2-methoxyethyl)piperazin-1-yl)propyl)-2-phenyl-N-(2-(thiazolo[5,4-b]pyridin-2-yl)phenyl)thiazole-4-carboxamide

HRID 1799133Notes

Reaction equation

HRID 1799133 reaction equation
Cl[CH2:2][CH2:3][CH2:4][C:5]1[S:9][C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[N:7][C:6]=1[C:16]([NH:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[C:25]1[S:26][C:27]2[C:32]([N:33]=1)=[CH:31][CH:30]=[CH:29][N:28]=2)=[O:17].[CH3:34][O:35][CH2:36][CH2:37][N:38]1[CH2:43][CH2:42][NH:41][CH2:40][CH2:39]1.O>CS(C)=O>[CH3:34][O:35][CH2:36][CH2:37][N:38]1[CH2:43][CH2:42][N:41]([CH2:2][CH2:3][CH2:4][C:5]2[S:9][C:8]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)=[N:7][C:6]=2[C:16]([NH:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[C:25]2[S:26][C:27]3[C:32]([N:33]=2)=[CH:31][CH:30]=[CH:29][N:28]=3)=[O:17])[CH2:40][CH2:39]1

Participants

5

Reactant 3

HCID 962WaterHCID 27346381-(2-Methoxyethyl)piperazineHCID 585518955-(3-chloropropyl)-2-phenyl-N-(2-(thiazolo[5,4-b]pyridin-2-yl)phenyl)thiazole-4-carboxamide

Product 1

HCID 462451305-(3-(4-(2-methoxyethyl)piperazin-1-yl)propyl)-2-phenyl-N-(2-(thiazolo[5,4-b]pyridin-2-yl)phenyl)thiazole-4-carboxamideYield 96%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 5-(3-chloropropyl)-2-phenyl-N-(2-(thiazolo[5,4-b]pyridin-2-yl)phenyl)thiazole-4-carboxamide (316 mg, 0.67 mmol) and 1-(2-methoxyethyl)-piperazine (964 mg, 6.7 mmol) in DMSO (12 mL) was heated at 70° C. for 16 h. The reaction mixture was cooled to room temperature and poured into H2O. The resulting solid was collected by filtration and rinsed with H2O. The crude product was purified by MPLC eluting with DCM/MeOH+1% TEA(0-10% gradient) to give the title compound (374 mg, 96% yield). MS Calcd for C32H34N6O2S2: 598.22. Found (M+H)+ m/z=599.

Workup

  1. filtrationThe resulting solid was collected by filtration
  2. washrinsed with H2O
  3. customThe crude product was purified by MPLC
  4. washeluting with DCM/MeOH+1% TEA(0-10% gradient)

Sources & evidence

ORD record
ord-e994903cfa1e400b8a27e758bdc2e166
Source dataset
uspto-grants-2013_01
Patent number
US08343997B2

Reaction notes

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