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 1756819노트

반응식

HRID 1756819 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-78f3a3584fb04af6bdf6cb37fd3abae8
출처 데이터셋
uspto-grants-1995_08
특허 번호
US05442077

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