Triethylamine → 4-Methoxy-7-morpholin-4-yl-benzothiazole-2-carboxylic acid (2-oxo-cyclohexyl)-amide

HRID 1244346Notes

Reaction equation

HRID 1244346 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.Cl.[NH2:34][CH:35]1[CH2:40][CH2:39][CH2:38][CH2:37][C:36]1=[O:41].C(N(CC)CC)C>CN(C)C=O.O>[O:41]=[C:36]1[CH2:37][CH2:38][CH2:39][CH2:40][CH:35]1[NH:34][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]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 112751042-Aminocyclohexan-1-one hydrochlorideHCID 219192164-Methoxy-7-morpholin-4-yl-benzothiazole-2-carboxylic acid

Product 1

HCID 865950064-Methoxy-7-morpholin-4-yl-benzothiazole-2-carboxylic acid (2-oxo-cyclohexyl)-amideYield 2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

6.00 g 4-Methoxy-7-morpholin-4-yl-benzothiazole-2-carboxylic acid and 3.75 g 1,1′-carbonyl-diimidazole in 360 ml dimethylformamide were stirred at room temperature for 16 hours. 3.36 g 2-amino-cyclohexanone hydrochloride and 3.14 ml triethylamine were added and stirring was continued over night at room temperature. Water was added and the mixture was extracted with ethylacetate. Chromatography on silicagel with ethylacetate/hexane 1:1 to yielded 0.16 g (2%) 4-methoxy-7-morpholin-4-yl-benzothiazole-2-carboxylic acid (2-oxo-cyclohexyl)-amide as a yellow solid; M.p.: 195–197° C.; MS (ISP): m/e=390 (M+H+).

Workup

  1. waitwas continued over night at room temperature
  2. extractionthe mixture was extracted with ethylacetate

Sources & evidence

ORD record
ord-46110ef1acfe4440bab6c502b70c61b7
Source dataset
uspto-grants-2006_10
Patent number
US07122545B2

Reaction notes

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