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

HRID 1244334Notes

Reaction equation

HRID 1244334 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[C:39]2[CH:46]=[CH:45][CH:44]=[CH:43][C:40]=2[S:41][CH:42]=1)=[O:37].C(N(CC)CC)C>CN(C=O)C.O>[S:41]1[CH:42]=[C:38]([C:36](=[O:37])[CH2:35][NH:34][C:12]([C:10]2[S:11][C:7]3[C:6]([N:15]4[CH2:20][CH2:19][O:18][CH2:17][CH2:16]4)=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[C:8]=3[N:9]=2)=[O:14])[C:39]2[CH:46]=[CH:45][CH:44]=[CH:43][C:40]1=2

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 219192164-Methoxy-7-morpholin-4-yl-benzothiazole-2-carboxylic acidHCID 219192602-Amino-1-benzo[b]thiophen-3-yl-ethanone hydrochloride

Product 1

HCID 865950044-Methoxy-7-morpholin-4-yl-benzothiazole-2-carboxylic acid (2-benzo[b]thiophen-3-yl-2-oxo-ethyl)-amideYield 44.1%

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 6 ml DMF were stirred at room temperature for 4 hours. 0.26 g 2-amino-1-benzo[b]thiophen-3-yl-ethanone hydrochloride and 0.–16 ml triethylamine were added and stirring was continued for two days at room temperature. 100 ml water was added and the mixture was extracted with ethylacetate. The precipitate was filtered to yield 0.21 g (44%) 4-methoxy-7-morpholin-4-yl-benzothiazole-2-carboxylic acid (2-benzo[b]thiophen-3-yl-2-oxo-ethyl)-amide as a yellow solid; M.p.: 256–258° C.; MS (ISP): m/e=468 (M+H+).

Workup

  1. extractionthe mixture was extracted with ethylacetate
  2. filtrationThe precipitate was filtered

Sources & evidence

ORD record
ord-8c2acf689c0d46e4a1acd6d4126dda66
Source dataset
uspto-grants-2006_10
Patent number
US07122545B2

Reaction notes

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