Hydrochloric Acid → HCID 178441076, compound

HRID 2081288Notes

Reaction equation

HRID 2081288 reaction equation
[CH2:1]([C:5]1[N:9]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[C:23]3[NH:27][N:26]=[N:25][N:24]=3)=[CH:13][CH:12]=2)[N:8]=[C:7]([C:28](O)=[O:29])[CH:6]=1)[CH2:2][CH2:3][CH3:4].P(C#N)(=O)(OCC)OCC.[Cl:41][C:42]1[CH:48]=[CH:47][C:45]([NH2:46])=[CH:44][CH:43]=1.Cl>CN(C=O)C.C(N(CC)CC)C>[CH2:1]([C:5]1[N:9]([CH2:10][C:11]2[CH:12]=[CH:13][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[C:23]3[NH:27][N:26]=[N:25][N:24]=3)=[CH:15][CH:16]=2)[N:8]=[C:7]([C:28]([NH:46][C:45]2[CH:47]=[CH:48][C:42]([Cl:41])=[CH:43][CH:44]=2)=[O:29])[CH:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 78124-ChloroanilineHCID 76257Diethyl cyanophosphonateHCID 178441097HCID 178441097, compound

Product 1

HCID 178441076HCID 178441076, compoundYield 38%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

A solution of 5-butyl-1-[[2'-(1H-tetrazol-5-yl)-biphenyl-4-yl]methyl]pyrazole-3-carboxylic acid (0.8 g) and diethyl phosphorocyanidate (90% purity, 0.76 g) in DMF (6 ml) was allowed to stir at 0°-5° C. for 1 hour. 4-Chloroaniline (0.25 g) and triethylamine (0.62 g) were added to the solution and the mixture was stirred at room temperature for 3 hours. The reaction solution was made acidic by addition of 1N-HCl and extracted with ethyl acetate. The organic layer was dried and evaporated to dryness to give a syrup. The syrup was purified by column chromatography on silica gel to give colorless powder (0.38 g, 38%),

Workup

  1. stirringthe mixture was stirred at room temperature for 3 hours
  2. extractionextracted with ethyl acetate
  3. customThe organic layer was dried
  4. customevaporated to dryness
  5. customto give a syrup
  6. customThe syrup was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-0ef5f2e0ce5d4445859ad57070e82365
Source dataset
uspto-grants-1993_02
Patent number
US05183899

Reaction notes

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