Pyridine → 8-bromo-N-(2-chloro-4-(dimethylcarbamoyl)phenyl)-4,5-dihydro-benzo[b]thieno[2,3-d]oxepine-2-carboxamide

HRID 627936

反応式

HRID 627936 の反応式
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:11]3[S:12][C:13]([C:15]([OH:17])=O)=[CH:14][C:10]=3[CH2:9][CH2:8][O:7][C:6]=2[CH:18]=1.[NH2:19][C:20]1[CH:30]=[CH:29][C:23]([C:24]([N:26]([CH3:28])[CH3:27])=[O:25])=[CH:22][C:21]=1[Cl:31].N1C=CC=CC=1>O=S(Cl)Cl.C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:11]3[S:12][C:13]([C:15]([NH:19][C:20]4[CH:30]=[CH:29][C:23]([C:24](=[O:25])[N:26]([CH3:27])[CH3:28])=[CH:22][C:21]=4[Cl:31])=[O:17])=[CH:14][C:10]=3[CH2:9][CH2:8][O:7][C:6]=2[CH:18]=1

参加物

6

反応物 3

HCID 1049PyridineHCID 202874814-Amino-3-chloro-N,N-dimethylbenzamideHCID 579001638-Bromo-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-2-carboxylic acid

生成物 1

HCID 568341578-bromo-N-(2-chloro-4-(dimethylcarbamoyl)phenyl)-4,5-dihydro-benzo[b]thieno[2,3-d]oxepine-2-carboxamide収率 77%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 24386Thionyl Chloride溶媒

実験手順

A solution of 8-bromo-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-2-carboxylic acid (25.00 g, 76.9 mmol) in SOCl2 (200 mL) was heated at 90-100° C. for 3 h. Concentration of the reaction mixture gave the crude acid chloride. A suspension of the acid chloride in THF (600 mL) was treated with a solution of 4-amino-3-chloro-N,N-dimethylbenzamide (18.23 g, 92.3 mmol) and pyridine (14 mL) in THF (200 mL) at 0° C. The mixture was allowed to reach room temperature and stirred overnight. After concentration, water (200 mL) was added into the mixture. The resulting precipitate was collected by filtration, washed with water and dried to give 8-bromo-N-(2-chloro-4-(dimethylcarbamoyl)phenyl)-4,5-dihydro-benzo[b]thieno[2,3-d]oxepine-2-carboxamide (29.88 g, yield: 77%). ESI-MS: 504.99. 1H NMR (DMSO-d6, 400 MHz): 610.14 (s, 1H, NH), 7.86 (s, 1H, ArH), 7.67-7.57 (m, 3H, ArH), 7.40-7.25 (m, 3H, ArH), 4.32 (t, J=5.2 Hz, 2H, CH2), 3.21 (t, J=5.2 Hz, 2H, CH2), 2.95 (s, 3H, CH3), 2.92 (s, 3H, CH3).

後処理

  1. customConcentration of the reaction mixture gave the crude acid chloride
  2. customto reach room temperature
  3. concentrationAfter concentration, water (200 mL)
  4. additionwas added into the mixture
  5. filtrationThe resulting precipitate was collected by filtration
  6. washwashed with water
  7. customdried

出典と根拠

ORDレコード
ord-3bd04d7b14a64ed08d2a41f2e01afbe3
出典データセット
uspto-grants-2016_04
特許番号
US09309265B2

関連ノート

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