Triethylamine → HCID 86595005, compound

HRID 1244344Notes

Reaction equation

HRID 1244344 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](=[O:43])[CH2:37][C:38]1[S:39][CH:40]=[CH:41][CH:42]=1.C(N(CC)CC)C>CN(C=O)C.O>[O:43]=[C:36]([CH2:37][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 219192164-Methoxy-7-morpholin-4-yl-benzothiazole-2-carboxylic acidHCID 21919256HCID 21919256, compound

Product 1

HCID 86595005HCID 86595005, compoundYield 18%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

0.41 g 4-Methoxy-7-morpholin-4-yl-benzothiazole-2-carboxylic acid and 0.14 g 1,1′-carbonyl-diimidazole in 11 ml DMF were stirred at room temperature for 16 hours. 0.16 g 1-amino-3-thiophen-2-yl-propan-2-one hydrochloride and 0.23 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 3:7–7:3 to yielded 0.06 g (18%) 4-methoxy-7-morpholin-4-yl-benzothiazole-2-carboxylic acid (2-oxo-3-thiophen-2-yl-propyl)-amide as a yellow solid; MS (ISP): m/e=432 (M+H+).

Workup

  1. extractionthe mixture was extracted with ethylacetate

Sources & evidence

ORD record
ord-7796e5aec5bc48acb9cb52b8a1d743fc
Source dataset
uspto-grants-2006_10
Patent number
US07122545B2

Reaction notes

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