Hydrochloric Acid → HCID 178441091, compound

HRID 2081286Notes

Reaction equation

HRID 2081286 reaction equation
ClN1C(=O)CCC1=O.[CH2:9]([C:13]1[N:17]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[C:31]3[NH:35][N:34]=[N:33][N:32]=3)=[CH:21][CH:20]=2)[N:16]=[C:15]([C:36]([OH:38])=[O:37])[CH:14]=1)[CH2:10][CH2:11][CH3:12].[F:39][C:40]([F:44])([F:43])[CH2:41]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.Cl>ClCCl.C(N(CC)CC)C>[CH2:9]([C:13]1[N:17]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[C:31]3[NH:32][N:33]=[N:34][N:35]=3)=[CH:21][CH:20]=2)[N:16]=[C:15]([C:36]([O:38][CH2:41][C:40]([F:44])([F:43])[F:39])=[O:37])[CH:14]=1)[CH2:10][CH2:11][CH3:12]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 64092,2,2-TrifluoroethanolHCID 11776Triphenylphosphine2×HCID 31398Chlorosuccinimide2×HCID 178441097HCID 178441097, compound

Product 1

HCID 178441091HCID 178441091, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

N-Chlorosuccinimide (400 mg) was added to a stirred solution of 5-butyl-1-[[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl]pyrazole-3-carboxylic acid (682 mg), triethylamine (1.2 g), 2,2,2-trifluoroethanol (248 mg) and triphenylphosphine (891 mg) in dichloromethane (30 ml) by cooling with an ice-bath. After stirring for 15 minutes, triphenylphosphine (262 mg) and N-chlorosuccinimide (133 mg) were added and the mixture was stirred for 30 minutes. After addition of 2N-hydrochloric acid (15 ml) and stirring at room temperature for 30 minutes, the mixture was allowed to separate into layers. The organic layer was washed with water, dried, and concentrated to dryness to give a syrup, which was then purified by column chromatography on silica gel, to give a yellow syrup (460 mg, 58%).

Workup

  1. temperatureby cooling with an ice-bath
  2. stirringthe mixture was stirred for 30 minutes
  3. stirringstirring at room temperature for 30 minutes
  4. customto separate into layers
  5. washThe organic layer was washed with water
  6. customdried
  7. concentrationconcentrated to dryness
  8. customto give a syrup, which
  9. customwas then purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-8f154a8774824f17b13696a4f11209a2
Source dataset
uspto-grants-1993_02
Patent number
US05183899

Reaction notes

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