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

HRID 1244341ノート

反応式

HRID 1244341 の反応式
[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]

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

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+).

後処理

  1. extractionthe mixture was extracted with ethylacetate

出典と根拠

ORDレコード
ord-68a2ba1c66dc44b7bf1ab781ed8ec933
出典データセット
uspto-grants-2006_10
特許番号
US07122545B2

反応ノート

読み込み中…