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2-(Dimethylamino)ethanol → N-[1,4-Dihydro-1-phenyl-3-(2-phenylcarbamoyl-cyanoacetyl)-indeno[1,2-c]pyrazol-7-yl]carbonyl-glycine methyl ester

HRID 21547
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HRID 21547 반응식
Cl.[CH3:2][O:3][C:4](=[O:7])[CH2:5][NH2:6].[C:8]([C:11]1[CH:42]=[C:41]2[C:14]([CH2:15][C:16]3[C:20]([C:21](=[O:34])[CH:22]([C:32]#[N:33])[C:23]([NH:25][C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)=[O:24])=[N:19][N:18]([C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)[C:17]=32)=[CH:13][CH:12]=1)(O)=[O:9].C1(N=C=NC2CCCCC2)CCCCC1.CN(CCO)C>C(#N)C.C(N(CC)CC)C>[CH3:2][O:3][C:4](=[O:7])[CH2:5][NH:6][C:8]([C:11]1[CH:42]=[C:41]2[C:14]([CH2:15][C:16]3[C:20]([C:21](=[O:34])[CH:22]([C:32]#[N:33])[C:23](=[O:24])[NH:25][C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)=[N:19][N:18]([C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)[C:17]=32)=[CH:13][CH:12]=1)=[O:9]
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참가 물질

7

반응물 4

HCID 79022-(Dimethylamino)ethanolHCID 10868DicyclohexylcarbodiimideHCID 122755Glycine methyl ester hydrochlorideHCID 199325823-(7-carboxy-1,4-dihydro-1-phenyl-indeno[1,2-c]pyrazole-3-yl)-2-cyano-3-oxo-N-phenyl-propanamide

생성물 1

HCID 19932613N-[1,4-Dihydro-1-phenyl-3-(2-phenylcarbamoyl-cyanoacetyl)-indeno[1,2-c]pyrazol-7-yl]carbonyl-glycine methyl ester
수율 45.2%

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 8471Triethylamine용매

실험 절차

Glycine methyl ester hydrochloride (0.7 g) suspended in anhydrous acetonitrile (250 ml) is treated with triethylamine (0.56 g) under stirring at room temperature. To the suspension first 3-(7-carboxy-1,4-dihydro-1-phenyl-indeno[1,2-c]pyrazole-3-yl)-2-cyano-3-oxo-N-phenyl-propanamide (2.3 g) and the dicyclohexylcarbodiimide (1.25 g) are added. The reaction mixture is kept under stirring at room temperature for 4 hours and then is basified to pH 8 by adding dimethylaminoethanol. The precipitate is filtered, washed with acetonitrile and then eliminated. The organic solution is concentrated in vacuo to a small volume, diluted with water, acidified to pH 2 with 1N HCl and then basified to pH 8 with 1N NaOH. The obtained precipitate is filtered, washed with water, dissolved in chloroform and washed with 1N HCl and then with water until neutral. The organic solution is evaporated in vacuo to dryness and the residue is purified over a SiO2 column using CHCl3 /methanol 90/10 as eluent. Final crystallization from CH2Cl 2 /ethyl acetate yields 1.2 g of pure N-[1,4-dihydro-1-phenyl-3-(2-phenylcarbamoyl-cyano-acetyl)indeno[1,2-c]pyrazol-7-yl] carbonyl-glycine methyl ester.

후처리

  1. stirringunder stirring at room temperature for 4 hours
  2. filtrationThe precipitate is filtered
  3. washwashed with acetonitrile
  4. concentrationThe organic solution is concentrated in vacuo to a small volume
  5. additiondiluted with water
  6. filtrationThe obtained precipitate is filtered
  7. washwashed with water
  8. dissolutiondissolved in chloroform
  9. washwashed with 1N HCl
  10. customThe organic solution is evaporated in vacuo to dryness
  11. customthe residue is purified over a SiO2 column
  12. customFinal crystallization from CH2Cl 2 /ethyl acetate

출처 및 근거

ORD 기록
ord-2598f6daf4df481c9a30d0b6858e1812
출처 데이터셋
uspto-grants-1995_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05424308

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