Acetic Acid → N-{2-(2-Cyano-3-oxobut-1-en-1-yl)furo[3,2-c]pyridin-4-yl}benzamide

HRID 1910661ノート

反応式

HRID 1910661 の反応式
[CH:1]([C:3]1[O:11][C:10]2[CH:9]=[CH:8][N:7]=[C:6]([NH:12][C:13](=[O:20])[C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:5]=2[CH:4]=1)=O.[C:21](/[CH:23]=[C:24](\[O-:26])/[CH3:25])#[N:22].[Na+].C(O)(=O)C.N1CCCCC1.C(=O)(O)[O-].[Na+]>ClCCl>[C:21]([C:23]([C:24](=[O:26])[CH3:25])=[CH:1][C:3]1[O:11][C:10]2[CH:9]=[CH:8][N:7]=[C:6]([NH:12][C:13](=[O:20])[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:5]=2[CH:4]=1)#[N:22]

参加物

7

反応物 5

HCID 176Acetic AcidHCID 8082PiperidineHCID 516892Sodium BicarbonateHCID 23687916sodium (1Z)-1-cyanoprop-1-en-2-olateHCID 86685438HCID 86685438、化合物

生成物 1

HCID 67154537N-{2-(2-Cyano-3-oxobut-1-en-1-yl)furo[3,2-c]pyridin-4-yl}benzamide収率 80.4%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A mixture of 1.50 g (5.63 mmol) N-(2-formylfuro[3,2-c]pyridin-4-yl)benzamide (Example 3A), 0.65 g (6.2 mmol) sodium (1Z)-1-cyanoprop-1-en-2-olate, 0.4 ml (7.04 mmol) acetic acid and 56 μl (0.56 mmol) piperidine in dry dichloromethane (35 ml) containing 4 Å molecular sieve was stirred under reflux for 1 h. After cooling, 50 ml aq. sodium bicarbonate solution were added, and the mixture was stirred for 1 h at rt. The molecular sieve was filtered off, and the filtrate was concentrated under reduced pressure. The residue was treated with ethyl acetate and saturated aq. sodium carbonate solution. The organic layer was separated, washed with water, dried, and concentrated under reduced pressure to afford the title compound (1.5 g, 80% of th.) as a pale yellow solid which was used in the next step without further purification.

後処理

  1. additioncontaining 4 Å molecular sieve
  2. temperatureunder reflux for 1 h
  3. temperatureAfter cooling
  4. stirringthe mixture was stirred for 1 h at rt
  5. filtrationThe molecular sieve was filtered off
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. additionThe residue was treated with ethyl acetate and saturated aq. sodium carbonate solution
  8. customThe organic layer was separated
  9. washwashed with water
  10. customdried
  11. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-e5730b6092fa49dea6cdacce2a9cf538
出典データセット
uspto-grants-2013_12
特許番号
US08604028B2

反応ノート

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