Triethylamine → 4-Methoxy-7-morpholin-4-yl-benzothiazole-2-carboxylic acid [2-(3-methyl-benzo[b]thiophen-2-yl)-2-oxo-ethyl]-amide

HRID 1244341Notes

Reaction equation

HRID 1244341 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[S:42][C:41]2[CH:43]=[CH:44][CH:45]=[CH:46][C:40]=2[C:39]=1[CH3:47])=[O:37].C(N(CC)CC)C>CN(C=O)C.O>[CH3:47][C:39]1[C:40]2[CH:46]=[CH:45][CH:44]=[CH:43][C:41]=2[S:42][C:38]=1[C:36](=[O:37])[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 219192164-Methoxy-7-morpholin-4-yl-benzothiazole-2-carboxylic acidHCID 219192252-Amino-1-(3-methyl-benzo[b]thiophen-2-yl)-ethanone hydrochloride

Product 1

HCID 211370764-Methoxy-7-morpholin-4-yl-benzothiazole-2-carboxylic acid [2-(3-methyl-benzo[b]thiophen-2-yl)-2-oxo-ethyl]-amideYield 24.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

0.30 g 4-Methoxy-7-morpholin-4-yl-benzothiazole-2-carboxylic acid and 0.19 g 1,1′-carbonyl-diimidazole in 18 ml DMF were stirred at room temperature for 4 hours. 0.27 g 2-amino-1-(3-methyl-benzo[b]thiophen-2-yl)-ethanone hydrochloride and 0.16 ml triethylamine were added and stirring was continued for two days at room temperature. Water was added and the mixture was extracted with ethylacetate. Chromatography on silicagel with ethylacetate/hexane 4:6 yielded 0.12 g (23%) 4-methoxy-7-morpholin-4-yl-benzothiazole-2-carboxylic acid [2-(3-methyl-benzo[b]thiophen-2-yl)-2-oxo-ethyl]-amide as a yellow solid; M.p.: 186–187° C.; MS (ISP): m/e=482 (M+H+).

Workup

  1. extractionthe mixture was extracted with ethylacetate

Sources & evidence

ORD record
ord-68a2ba1c66dc44b7bf1ab781ed8ec933
Source dataset
uspto-grants-2006_10
Patent number
US07122545B2

Reaction notes

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