Triethylamine → 3-chloro-N-[3-(2'-oxospiro[furo[2,3-f][1,3]benzodioxole-7,3'-indol]-1'(2'H)-yl)propyl]thiophene-2-carboxamide

HRID 425712

反応式

HRID 425712 の反応式
[NH2:1][CH2:2][CH2:3][CH2:4][N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]2([C:17]3=[CH:18][C:19]4[O:23][CH2:22][O:21][C:20]=4[CH:24]=[C:16]3[O:15][CH2:14]2)[C:6]1=[O:25].C(N(CC)CC)C.[Cl:33][C:34]1[CH:38]=[CH:37][S:36][C:35]=1[C:39](Cl)=[O:40]>ClCCl>[Cl:33][C:34]1[CH:38]=[CH:37][S:36][C:35]=1[C:39]([NH:1][CH2:2][CH2:3][CH2:4][N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]2([C:17]3=[CH:18][C:19]4[O:23][CH2:22][O:21][C:20]=4[CH:24]=[C:16]3[O:15][CH2:14]2)[C:6]1=[O:25])=[O:40]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 27358243-Chlorothiophene-2-carbonyl chlorideHCID 119998911'-(3-aminopropyl)spiro[furo[2,3-f]-[1,3]benzodioxole-7,3'-indol]-2'(1'H)-one

生成物 1

HCID 592634603-chloro-N-[3-(2'-oxospiro[furo[2,3-f][1,3]benzodioxole-7,3'-indol]-1'(2'H)-yl)propyl]thiophene-2-carboxamide収率 69%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of 1′-(3-aminopropyl)spiro[furo[2,3-f][1,3]benzodioxole-7,3′-indol]-2′(1′H)-one (0.05 g, 0.13 mmol) in dichloromethane (4.00 mL) was added triethylamine (0.03 g, 0.26 mmol) and 3-chlorothiophene-2-carbonyl chloride (0.02 g, 0.12 mmol) at 0° C. The mixture was stirred for 2 h, washed with 15% HCl solution and water. The organic layer was dried over MgSO4 and filtered. The filtrate was concentrated in vacuo to dryness. The residue was dissolved in ethyl acetate, and the product was precipitated with the addition of hexane. The white solid was collected by filtration and dried in vacuo to yield the title compound (0.04 g) in 67% yield: 1H NMR (300 MHz, CDCl3) δ 7.60 (t, 1H), 7.41 (d, 1H), 7.33-7.27-(m, 1H), 7.17 (d, 1H), 7.08-7.03-(m, 1H), 6.93 (t, 1H), 6.49 (s, 1H), 6.11 (s, 1H), 5.95 (m, 2H), 4.90 (d, 1H), 4.65 (d, 1H), 3.96-3.79-(m, 2H), 3.53-3.36-(m, 2H), 2.04-1.93-(m, 2H); 13C NMR (75 MHz, CDCl3) δ 178.3, 160.6, 156.0, 149.0, 142.4, 141.8, 132.5, 129.4, 129.2, 129.1, 124.2, 123.7, 123.6, 119.2, 108.5, 102.9, 101.6, 93.7, 80.5, 58.3, 37.4, 36.5, 27.3; MS (ES+) m/z 483 (M+1).

後処理

  1. washwashed with 15% HCl solution and water
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated in vacuo to dryness
  5. dissolutionThe residue was dissolved in ethyl acetate
  6. customthe product was precipitated with the addition of hexane
  7. filtrationThe white solid was collected by filtration
  8. customdried in vacuo

出典と根拠

ORDレコード
ord-38af02eaecf246b99246071bebe244b8
出典データセット
uspto-grants-2012_01
特許番号
US08106087B2

関連ノート

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