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

HRID 1244330Notes

Reaction equation

HRID 1244330 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][CH2:35][C:36]([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)=[O:37].C(N(CC)CC)C>CN(C=O)C.O>[O:37]=[C:36]([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[CH2:35][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 2723597Ethanone, 2-amino-1-phenyl-, hydrochloride (1:1)HCID 219192164-Methoxy-7-morpholin-4-yl-benzothiazole-2-carboxylic acid

Product 1

HCID 211370664-Methoxy-7-morpholin-4-yl-benzothiazole-2-carboxylic acid (2-oxo-2-phenyl-ethyl)-amideYield 64.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

0.20 g 4-Methoxy-7-morpholin-4-yl-benzothiazole-2-carboxylic acid and 0.125 g 1,1′-carbonyl-diimidazole in 1 ml DMF were stirred at room temperature for 1 hour. 0.13 g 2-aminoacetophenone hydrochloride and 0.08 g triethylamine were added and stirring was continued for two days at room temperature. 200 ml water was added and the mixture was extracted with ethylacetate. Chromatography on silicagel with ethylacetate/hexane 4:6 yielded 0.18 g (64%) 4-methoxy-7-morpholin-4-yl-benzothiazole-2-carboxylic acid (2-oxo-2-phenyl-ethyl)-amide as a yellow solid; M.p.: 197–200° C.; MS (ISP): m/e=412 (M+H+).

Workup

  1. extractionthe mixture was extracted with ethylacetate

Sources & evidence

ORD record
ord-b1b67c0c831d4f00aa761ad6fb77f8f8
Source dataset
uspto-grants-2006_10
Patent number
US07122545B2

Reaction notes

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