Methyl Isocyanate → HCID 14183052, compound
Reaction equation
[F:1][C:2]([F:25])([F:24])[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][NH:21][CH2:20][CH2:19]3)=[N:10]2)=[CH:5][CH:4]=1.[CH3:26][N:27]=[C:28]=[O:29]>C1(C)C=CC=CC=1>[CH3:26][NH:27][C:28]([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:24])[F:25])=[CH:4][CH:5]=3)[N:10]=2)[CH2:23][CH2:22]1)=[O:29]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A stirred mixture of 4-[1-(4-(trifluoromethyl)phenyl)-1H-indazol-3-yl]piperidine-1-carbonitrile of Example 101 (15 g, 0.041 moles) and 25% H2SO4 (100 ml) was refluxed for 20 hours. The mixture was cooled. poured into H2O and basified with a 25% NaOH solution. The product was extracted (dichloromethane), dried (MgSO4), and concentrated to yield 13 g (93%) of 1-[4-(trifluoromethyl)phenyl]-3-(4-piperidinyl)-1H-indazole as an oil. To a stirred suspension of the indazole (4.0 g, 0.012 moles) in toluene (60 ml) was added methyl isocyanate (0.75 ml., 0.013 moles). The temperature of the reaction mixture rose to 35° C. following the addition. The mixture was stirred for 2 hours at ambient temperature and then concentrated to yield 4.6 g of a solid. The product was purified by high pressure liquid chromatography (3.5% methanol-CHCl3 ; silica gel) and then recrystallized three times from toluene-hexane to yield 2.93 g (63%) of N-methyl-4-[1-(4-trifluoromethyl)phenyl]-1H-indazol-3-yl]piperidine-1-carboxamide, m.p.: 150°-152° C.
Workup
- customrose to 35° C.
- additionthe addition
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-1f4193d8fcc84793afd23be43646e4e8
- Source dataset
- uspto-grants-1989_02
- Patent number
- US04806649
Reaction notes
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