4-Amino-5-chloro-2,3-dihydrobenzofuran-7-carboxylic acid → 4-Amino-N-[2-(1-azabicyclo[3.3.0]octan-5-yl)ethyl]-5-chloro-2,3-dihydrobenzo[b]furan-7-carboxamide

HRID 1756819ノート

反応式

HRID 1756819 の反応式
[NH2:1][C:2]1[C:10]2[CH2:9][CH2:8][O:7][C:6]=2[C:5]([C:11]([OH:13])=O)=[CH:4][C:3]=1[Cl:14].[NH2:15][CH2:16][CH2:17][C:18]12[CH2:25][CH2:24][CH2:23][N:22]1[CH2:21][CH2:20][CH2:19]2>O1CCCC1>[NH2:1][C:2]1[C:10]2[CH2:9][CH2:8][O:7][C:6]=2[C:5]([C:11]([NH:15][CH2:16][CH2:17][C:18]23[CH2:19][CH2:20][CH2:21][N:22]2[CH2:23][CH2:24][CH2:25]3)=[O:13])=[CH:4][C:3]=1[Cl:14]

参加物

4

反応物 2

HCID 106324014-Amino-5-chloro-2,3-dihydrobenzofuran-7-carboxylic acidHCID 107969772-(Hexahydro-1H-pyrrolizin-7a-yl)ethanamine

生成物 1

HCID 105217924-Amino-N-[2-(1-azabicyclo[3.3.0]octan-5-yl)ethyl]-5-chloro-2,3-dihydrobenzo[b]furan-7-carboxamide収率 78.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

Into an agitating solution of 4-amino-5-chloro-2,3-dihydrobenzo[b]furan-7-carboxylic acid (3.21 g) in absolute tetrahydrofuran (50 ml), was added little by little 1,1-carbonylimidazole (2.43 g) and after lapsed 1 hour, a solution of 5-(2-aminoethyl)-1-azabicyclo[3.3.0]octane (2.31 g) in absolute tetrahydrofuran (2 ml) was added therein to reflux for 1 hour. After cooled, the solvent was distilled out in vacuo, a residue was dissolved into chloroform, washed with saturated sodium hydrogen carbonate solution and then water, and thereafter, the solvent was distilled out in vacuo. The resulting residue was refined by alumina column chromatography (developing solvent: chloroform) to afford 4.1 g of the titled compound.

後処理

  1. temperatureto reflux for 1 hour
  2. temperatureAfter cooled
  3. distillationthe solvent was distilled out in vacuo
  4. dissolutiona residue was dissolved into chloroform
  5. washwashed with saturated sodium hydrogen carbonate solution
  6. distillationwater, and thereafter, the solvent was distilled out in vacuo

出典と根拠

ORDレコード
ord-78f3a3584fb04af6bdf6cb37fd3abae8
出典データセット
uspto-grants-1995_08
特許番号
US05442077

反応ノート

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