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

反応式

HRID 21547 の反応式
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]

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒HCID 8471Triethylamine溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-2598f6daf4df481c9a30d0b6858e1812
出典データセット
uspto-grants-1995_06
特許番号
US05424308

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