Water → HCID 14032642, compound

HRID 652185Notes

Reaction equation

HRID 652185 reaction equation
[F:1][C:2]([F:27])([F:26])[C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]([CH:18]3[CH2:23][CH2:22][N:21]([C:24]#[N:25])[CH2:20][CH2:19]3)=[N:10]2)=[CH:5][CH:4]=1.[CH3:28][O-:29].[Na+].O>CO>[CH3:28][O:29][C:24]([N:21]1[CH2:20][CH2:19][CH:18]([C:11]2[C:12]3[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=3)[N:9]([C:6]3[CH:7]=[CH:8][C:3]([C:2]([F:1])([F:26])[F:27])=[CH:4][CH:5]=3)[N:10]=2)[CH2:23][CH2:22]1)=[NH:25]

Participants

5

Reactant 3

HCID 962WaterHCID 10942334Sodium MethoxideHCID 14032656HCID 14032656, compound

Product 1

HCID 14032642HCID 14032642, compoundYield 87.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 4-[1-(4-trifluoromethylphenyl)-1H-indazol-3-yl]-piperidine-1-carbonitrile of Example 101 (20.0 g, 0.054 moles) and sodium methoxide (12.4 ml of 25% sodium methoxide in methanol 0.054 moles) in methanol (120 ml) was warmed to effect solution and then stirred at ambient temperature for 3 hours. The mixture was poured into H2O, extracted (CHCl3), dried (MgSO4), and concentrated to yield an oil. The oil was triturated with hexane which produced 19 g of a solid. The solid was recrystallized twice from toluene-hexane which yielded 14.2 g (65%) of 4-[1-[4-trifluoromethyl)phenyl]-1H-indazol-3-yl]piperidine-1-carboximidic acid methyl ester, m.p. 113°-115° C.

Workup

  1. temperaturewas warmed
  2. extractionextracted (CHCl3)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customto yield an oil
  6. customThe oil was triturated with hexane which

Sources & evidence

ORD record
ord-e09281c9573249b9a8a3e6225694a823
Source dataset
uspto-grants-1987_06
Patent number
US04670447

Reaction notes

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