Sodium Hydroxide → 2-(1,1-Dioxido-2,3-dihydro-1,4-benzothiazepin-4(5H)-yl)-6-methylquinolin-4-amine

HRID 540162ノート

反応式

HRID 540162 の反応式
[O:1]=[S:2]1(=[O:25])[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[CH2:6][N:5](/[C:13](=[N:15]/[C:16]2[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][C:17]=2[C:18]#[N:19])/[CH3:14])[CH2:4][CH2:3]1.CN(C)C(=O)C.[OH-].[Na+]>[Cl-].[Zn+2].[Cl-].O>[O:25]=[S:2]1(=[O:1])[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[CH2:6][N:5]([C:13]2[CH:14]=[C:18]([NH2:19])[C:17]3[C:16](=[CH:23][CH:22]=[C:21]([CH3:24])[CH:20]=3)[N:15]=2)[CH2:4][CH2:3]1

参加物

6

反応物 3

HCID 14798Sodium HydroxideHCID 31374DimethylacetamideHCID 178463280HCID 178463280、化合物

生成物 1

HCID 712554832-(1,1-Dioxido-2,3-dihydro-1,4-benzothiazepin-4(5H)-yl)-6-methylquinolin-4-amine収率 100.1%

試薬・触媒・溶媒 2

HCID 3007855Zincchloride触媒HCID 962Water溶媒

反応条件

温度
160 °C

実験手順

A mixture of 2-{[(1E)-1-(1,1-dioxido-2,3-dihydro-1,4-benzothiazepin-4(5H)-yl)ethylidene]amino}-5-methylbenzonitrile (1.5 g, 4.24 mmol), zinc chloride (578 mg, 4.24 mmol) and N,N-dimethylacetamide (4 mL) was heated with stirring at 160° C. for 3 hours under argon. After the reaction mixture was cooled to about 40° C., an aqueous solution of sodium hydroxide (2 N, 20 mL) was introduced. After being stirred for 10 minutes at room temperature, the reaction mixture was poured into water. The formed solid was collected by filtration, and dried in vacuo to give 1.5 g of the product as a brown powder. MS obsd. (ESI+) [(M+H)+] 354, 1H NMR (400 MHz, DMSO-d6) δ ppm 7.90-7.84 (m, 2 H), 7.66-7.62 (m, 2 H), 7.48 (t, J=7.2 Hz, 1 H), 7.32 (d, J=8.4 Hz, 1 H), 7.23 (dd, J=1.6, 8.8 Hz, 1 H), 6.29 (s, 2 H), 6.23 (s, 1 H), 4.97 (s, 2 H), 4.36 (brs, 2 H), 3.60 (t, J=4.8 Hz, 2 H), 2.34 (s, 3 H).

後処理

  1. temperaturewas heated
  2. temperatureAfter the reaction mixture was cooled to about 40° C.
  3. stirringAfter being stirred for 10 minutes at room temperature
  4. filtrationThe formed solid was collected by filtration
  5. customdried in vacuo

出典と根拠

ORDレコード
ord-c57002fbdf4446b49f5f7b93f51ced83
出典データセット
uspto-grants-2014_10
特許番号
US08871756B2

反応ノート

読み込み中…