2-Methyl-2-butene → 1-Ethyl-3-propyl-4-[[2'-[[(trifluoromethyl)sulphonyl]amino][1,1'-biphenyl]-4-yl]methyl]-1H-pyrazole-5-carboxylic acid

HRID 274599Notes

Reaction equation

HRID 274599 reaction equation
Cl([O-])=O.[Na+].P([O-])(O)(O)=[O:6].[Na+].[CH2:11]([N:13]1[C:17]([CH:18]=[O:19])=[C:16]([CH2:20][C:21]2[CH:26]=[CH:25][C:24]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[NH:33][S:34]([C:37]([F:40])([F:39])[F:38])(=[O:36])=[O:35])=[CH:23][CH:22]=2)[C:15]([CH2:41][CH2:42][CH3:43])=[N:14]1)[CH3:12].CC(=CC)C>O.C(O)(C)(C)C.C1COCC1>[CH2:11]([N:13]1[C:17]([C:18]([OH:6])=[O:19])=[C:16]([CH2:20][C:21]2[CH:22]=[CH:23][C:24]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[NH:33][S:34]([C:37]([F:38])([F:40])[F:39])(=[O:35])=[O:36])=[CH:25][CH:26]=2)[C:15]([CH2:41][CH2:42][CH3:43])=[N:14]1)[CH3:12]

Participants

8

Reactant 4

HCID 105532-Methyl-2-buteneHCID 20093388N-[4'-[[1-Ethyl-5-formyl-3-propyl-1H-pyrazol-4-yl]methyl][1,1'-biphenyl]-2-yl]trifluoromethanesulphonamideHCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphate

Product 1

HCID 200933151-Ethyl-3-propyl-4-[[2'-[[(trifluoromethyl)sulphonyl]amino][1,1'-biphenyl]-4-yl]methyl]-1H-pyrazole-5-carboxylic acidYield 56.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6386tert-ButanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of sodium chlorite (0.4 g) and sodium dihydrogen orthophosphate (2.56 g) in water (5 ml) was added to a solution of the product of Example 88 (430 mg) and 2-methyl-2-butene (4.5 ml, 2M solution in THF) in t-butanol (5 ml) and THF (10 ml) and the resulting mixture stirred for 3 h. Solvent was removed in vacuo, the residue taken up in dichloromethane (10 ml) and washed with water (10 ml). 2N Sodium hydroxide (10 ml) was added to the organic solution and the organic layer removed. 2N Hydrochloric acid (~11 ml) was added to the aqueous phase which was then extracted with ethyl acetate (2×15 ml). The dried organic extracts were evaporated in vacuo to give a yellow gummy solid which was recrystaltised from System D (1:1) to give the title compound as a white solid (250 mg) m.p. 68°-72° C.

Workup

  1. customSolvent was removed in vacuo
  2. washwashed with water (10 ml)
  3. addition2N Sodium hydroxide (10 ml) was added to the organic solution
  4. customthe organic layer removed
  5. addition2N Hydrochloric acid (~11 ml) was added to the aqueous phase which
  6. extractionwas then extracted with ethyl acetate (2×15 ml)
  7. customThe dried organic extracts were evaporated in vacuo
  8. customto give a yellow gummy solid which

Sources & evidence

ORD record
ord-832daeb6959749d0885e9f6450ad82d3
Source dataset
uspto-grants-1995_02
Patent number
US05389659

Reaction notes

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