Potassium Carbonate → {4-Methoxy-7-[(pyridin-2-ylmethyl)-amino]-benzothiazol-2-yl}-carbamic acid methyl ester

HRID 51858

反応式

HRID 51858 の反応式
[CH3:1][O:2][C:3](=[O:17])[NH:4][C:5]1[S:6][C:7]2[C:13]([NH2:14])=[CH:12][CH:11]=[C:10]([O:15][CH3:16])[C:8]=2[N:9]=1.C(=O)([O-])[O-].[K+].[K+].Br.Br[CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=1>>[CH3:1][O:2][C:3](=[O:17])[NH:4][C:5]1[S:6][C:7]2[C:13]([NH:14][CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=3)=[CH:12][CH:11]=[C:10]([O:15][CH3:16])[C:8]=2[N:9]=1

参加物

4

反応物 3

HCID 11430Potassium CarbonateHCID 27347202-(Bromomethyl)pyridine hydrobromideHCID 21303404(7-Amino-4-methoxy-benzothiazol-2-yl)-carbamic acid methyl ester

生成物 1

HCID 86589018{4-Methoxy-7-[(pyridin-2-ylmethyl)-amino]-benzothiazol-2-yl}-carbamic acid methyl ester収率 37%

反応条件

温度
70 °C

実験手順

To a stirred solution of 40 mg (0.16 mmol) (7-amino-4-methoxy-benzothiazol-2-yl)-carbamic acid methyl ester in 2 ml DM F at room temperature were added 66 mg (0.47 mmol) potassium carbonate and 40 mg (0.16 mmol) 2-(bromomethyl)pyridine hydrobromide and the mixture heated at 70° C. for 16 h. The mixture was then concentrated in vacuo. Flash chromatography (2/1 ethyl acetate/hexane) afforded 20 mg (37%) {4-methoxy-7-[(pyridin-2-ylmethyl)-amino]-benzothiazol-2-yl}-carbamic acid methyl ester as a yellow solid. ES-MS m/e (%): 367 (M+Na+, 54), 345 (M+H+, 100).

後処理

  1. concentrationThe mixture was then concentrated in vacuo

出典と根拠

ORDレコード
ord-40b3682103a84d0d8b4476b232c7de3d
出典データセット
uspto-grants-2004_03
特許番号
US06713499B2

関連ノート

読み込み中…