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

HRID 1244336Notes

Reaction equation

HRID 1244336 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:39][CH:40]=[CH:41][CH:42]=1)=[O:37].C(N(CC)CC)C>CN(C=O)C.O>[O:37]=[C:36]([C:38]1[S:39][CH:40]=[CH:41][CH:42]=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 126098332-Amino-1-(thiophen-2-yl)ethan-1-one hydrochlorideHCID 219192164-Methoxy-7-morpholin-4-yl-benzothiazole-2-carboxylic acid

Product 1

HCID 211370564-Methoxy-7-morpholin-4-yl-benzothiazole-2-carboxylic acid (2-oxo-2-thiophen-2-yl-ethyl)-amideYield 44.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

0.40 g 4-Methoxy-7-morpholin-4-yl-benzothiazole-2-carboxylic acid and 0.25 g 1,1′-carbonyl-diimidazole in 40 ml DMF were stirred at room temperature for 1.5 hours. 0.27 g 2-amino-1-(2-thienyl)ethanone hydrochloride and 0.15 g triethylamine were added and stirring was continued over night at room temperature. 350 ml water was added and the mixture was extracted with ethylacetate. Chromatography on silicagel with ethylacetate/hexane 4:6 yielded 0.25 g (43%) 4-methoxy-7-morpholin-4-yl-benzothiazole-2-carboxylic acid (2-oxo-2-thiophen-2-yl-ethyl)-amide as a yellow solid; MS (ISP): m/e=418 (M+H+).

Workup

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

Sources & evidence

ORD record
ord-e46bb1c0f50b42e594dcab4a42fe767b
Source dataset
uspto-grants-2006_10
Patent number
US07122545B2

Reaction notes

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