Hydrochloric Acid → N-[1,4-dihydro-1-phenyl-3-(2-phenylcarbamoyl-cyanoacetyl)-indeno[1,2-c]pyrazol-7-yl]carbonyl glycine

HRID 21548Notes

Reaction equation

HRID 21548 reaction equation
C[O:2][C:3](=[O:40])[CH2:4][NH:5][C:6]([C:8]1[CH:39]=[C:38]2[C:11]([CH2:12][C:13]3[C:17]([C:18](=[O:31])[CH:19]([C:29]#[N:30])[C:20](=[O:28])[NH:21][C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)=[N:16][N:15]([C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)[C:14]=32)=[CH:10][CH:9]=1)=[O:7].Cl>[OH-].[K+].C(O)C>[C:32]1([N:15]2[C:14]3[C:38]4[C:11]([CH2:12][C:13]=3[C:17]([C:18](=[O:31])[CH:19]([C:29]#[N:30])[C:20](=[O:28])[NH:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[N:16]2)=[CH:10][CH:9]=[C:8]([C:6]([NH:5][CH2:4][C:3]([OH:40])=[O:2])=[O:7])[CH:39]=4)[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 19932613N-[1,4-Dihydro-1-phenyl-3-(2-phenylcarbamoyl-cyanoacetyl)-indeno[1,2-c]pyrazol-7-yl]carbonyl-glycine methyl ester

Product 1

HCID 53740921N-[1,4-dihydro-1-phenyl-3-(2-phenylcarbamoyl-cyanoacetyl)-indeno[1,2-c]pyrazol-7-yl]carbonyl glycineYield 79.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14797Potassium HydroxideSolvent

Procedure

N-[1,4-Dihydro-1-phenyl-3-(2-phenylcarbamoyl-cyanoacetyl) -indeno[1,2-c]pyrazol-7-yl]carbonyl-glycine methyl ester (0.84 g) is suspended in 1% KOH solution in 95% ethanol (22.3 ml) and heated under stirring at the reflux temperature for 30 minutes. After cooling the reaction mixture is acidified to pH 2 with 23% HCl and then diluted with ice water. The precipitate is filtered, washed with water and then crystallized from CH2Cl2 /ethanol to yield 0.65 g of pure N-[1,4-dihydro-1-phenyl-3-(2-phenylcarbamoyl-cyanoacetyl) -indeno[1,2-c]pyrazol-7-yl]carbonyl glycine.

Workup

  1. temperatureheated
  2. temperatureAfter cooling the reaction mixture
  3. filtrationThe precipitate is filtered
  4. washwashed with water
  5. customcrystallized from CH2Cl2 /ethanol

Sources & evidence

ORD record
ord-f563a5c258a7473ab324998b4fa80bf7
Source dataset
uspto-grants-1995_06
Patent number
US05424308

Reaction notes

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