Triethylamine → HCID 21137090, compound

HRID 1244332Notes

Reaction equation

HRID 1244332 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:47]=[CH:46][C:41]2[O:42][CH2:43][CH2:44][O:45][C:40]=2[CH:39]=1)=[O:37].C(N(CC)CC)C>CN(C=O)C.O>[O:42]1[C:41]2[CH:46]=[CH:47][C:38]([C:36](=[O:37])[CH2:35][NH:34][C:12]([C:10]3[S:11][C:7]4[C:6]([N:15]5[CH2:20][CH2:19][O:18][CH2:17][CH2:16]5)=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[C:8]=4[N:9]=3)=[O:14])=[CH:39][C:40]=2[O:45][CH2:44][CH2:43]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 168060522-Amino-1-(2,3-dihydro-1,4-benzodioxin-6-yl)ethan-1-one--hydrogen chloride (1/1)HCID 219192164-Methoxy-7-morpholin-4-yl-benzothiazole-2-carboxylic acid

Product 1

HCID 21137090HCID 21137090, compoundYield 50.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

0.35 g 4-Methoxy-7-morpholin-4-yl-benzothiazole-2-carboxylic acid and 0.22 g 1,1′-carbonyl-diimidazole in 6 ml DMF were stirred at room temperature for 4 hours. 0.30 g 2-amino-1-(2,3-dihydro-benzo[1,4]dioxin-6-yl)-ethanone hydrochloride and 0.18 g triethylamine were added and stirring was continued over night at room temperature. 100 ml water was added and the mixture was extracted with ethylacetate. Chromatography on silicagel with ethylacetate/hexane 1:1 yielded 0.28 g (50%) 4-methoxy-7-morpholin-4-yl-benzothiazole-2-carboxylic acid [2-(2,3-dihydro-benzo[1,4]dioxin-6-yl)-2-oxo-ethyl]-amide as a yellow solid; M.p.: 206–208° C.; MS (ISP): m/e=470 (M+H+).

Workup

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

Sources & evidence

ORD record
ord-09ba02447a264217bb5e13f3244264d7
Source dataset
uspto-grants-2006_10
Patent number
US07122545B2

Reaction notes

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