Water → 4-Methoxy-7-morpholin-4-yl-benzothiazole-2-carboxylic acid benzylamide

HRID 1358237Notes

Reaction equation

HRID 1358237 reaction equation
[CH3:1][O:2][C:3]1[C:8]2[N:9]=[C:10]([C:12]([OH:14])=O)[S:11][C:7]=2[C:6]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)=[CH:5][CH:4]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[CH2:33]([NH2:40])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.O>CN(C)C=O>[CH2:33]([NH:40][C:12]([C:10]1[S:11][C:7]2[C:6]([N:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[C:8]=2[N:9]=1)=[O:14])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7504BenzylamineHCID 682631,1'-CarbonyldiimidazoleHCID 219192164-Methoxy-7-morpholin-4-yl-benzothiazole-2-carboxylic acid

Product 1

HCID 692891714-Methoxy-7-morpholin-4-yl-benzothiazole-2-carboxylic acid benzylamideYield 81.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 29.4 mg (0.10 mmol) 4-methoxy-7-morpholin-4-yl-benzothiazole-2-carboxylic acid and 18.4 mg (0.11 mmol) 1.1′-carbonyl-diimidazole in 3 ml dimethylformamide was stirred at room temperature for one hour. 12.1 μl (0.11 mmol) benzylamine were added, stirring was continued and after 20 hours 15 ml water were added. Extraction with ethyl acetate and chromatography on silicagel with dichloromethane/ethyl acetate 95/5 yielded 31.2 mg (41%) of yellow 4-methoxy-7-morpholin-4-yl-benzothiazole-2-carboxylic acid benzylamide with mp.: 156-158° C., MS m/e (%): 384 (M+H+, 100).

Workup

  1. stirringstirring
  2. waitwas continued and after 20 hours
  3. extractionExtraction with ethyl acetate and chromatography on silicagel with dichloromethane/ethyl acetate 95/5

Sources & evidence

ORD record
ord-63021276852e4cd6a256684e3e968443
Source dataset
uspto-grants-2003_07
Patent number
US06596718B1

Reaction notes

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