Water → N-(2-chlorophenyl)-N-methyl-4,5-dihydropyrido[4,3-b]thieno[2,3-d]oxepin-2-carboxamide

HRID 1949731

反応式

HRID 1949731 の反応式
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][C:11]([C:13]1[S:26][C:16]2[C:17]3[CH:25]=[N:24][CH:23]=[CH:22][C:18]=3[O:19][CH2:20][CH2:21][C:15]=2[CH:14]=1)=[O:12].[CH3:27]I.O>O1CCCC1>[Cl:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]([CH3:27])[C:11]([C:13]1[S:26][C:16]2[C:17]3[CH:25]=[N:24][CH:23]=[CH:22][C:18]=3[O:19][CH2:20][CH2:21][C:15]=2[CH:14]=1)=[O:12]

参加物

6

反応物 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 57900340N-(2-chlorophenyl)-4,5-dihydropyrido[4,3-b]thieno[2,3-d]oxepin-2-carboxamide

生成物 1

HCID 44242495N-(2-chlorophenyl)-N-methyl-4,5-dihydropyrido[4,3-b]thieno[2,3-d]oxepin-2-carboxamide収率 67.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Sodium hydride, 60% dispersion in mineral oil (80 mg, 2.0 mmol) was added to a solution of N-(2-chlorophenyl)-4,5-dihydropyrido[4,3-b]thieno[2,3-d]oxepin-2-carboxamide (71.4 mg, 0.2 mmol) in 10 ml of tetrahydrofuran. The mixture was stirred for 30 min and mixed with methyl iodide (0.12 mL, 2.0 mmol). The reaction mixture was stirred for 1 hour. The mixture was mixed with 50 ml of iced water and extracted with ethyl acetate twice. The combined ethyl acetate solution was washed with brine, dried over MgSO4, concentrated in vacuo, and purified on silica gel column eluting with 25% of ethylacetate in methylene chloride to give 162 (yield 50 mg, 67%). 1H NMR (400 MHz, DMSO) δ 8.57 (s, 1H), 8.25 (d, J=5.5, 1H), 7.68 (t, J=5.9, 2H), 7.60-7.50 (m, 2H), 6.98 (d, J=5.5, 1H), 6.64 (s, 1H), 4.27 (m, 2H), 3.28 (s, 3H), 2.99 (m, 2H). MS (ESI+) 371.1

後処理

  1. stirringThe reaction mixture was stirred for 1 hour
  2. extractionextracted with ethyl acetate twice
  3. washThe combined ethyl acetate solution was washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. custompurified on silica gel column
  7. washeluting with 25% of ethylacetate in methylene chloride

出典と根拠

ORDレコード
ord-ee096e70ad374242bc98976fea99d5a3
出典データセット
uspto-grants-2013_03
特許番号
US08399690B2

関連ノート

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