Water → HCID 14032667, compound

HRID 986180Notes

Reaction equation

HRID 986180 reaction equation
Cl.[F:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([C:12]1[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=1)[N:7]=[C:6]2[CH:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1.[N+]([NH:31][C:32](N)=[O:33])([O-])=O.O>CN(C=O)C>[F:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([C:12]1[CH:13]=[CH:14][C:15]([C:18]([F:19])([F:20])[F:21])=[CH:16][CH:17]=1)[N:7]=[C:6]2[CH:22]1[CH2:27][CH2:26][N:25]([C:32]([NH2:31])=[O:33])[CH2:24][CH2:23]1

Participants

5

Reactant 3

HCID 962WaterHCID 62372NitroureaHCID 14032601HCID 14032601, compound

Product 1

HCID 14032667HCID 14032667, compoundYield 39.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-fluoro-1-[4-(trifluoromethyl)phenyl]-3-(4-piperidinyl)-1H-indazole free base of Example 124 (6.3 g, 0.017 moles) in DMF (100 ml) was added nitrourea (2.2 g, 0.021 moles). The mixture was warmed on a steam bath until gas began to evolve and was then stirred at ambient temperature for 4 hours. The mixture was then poured into H2O and the product extracted (dichloromethane), dried (MgSO4), and concentrated to yield 6.9 of an oil. The oil was triturated with water to produce 6.9 of a solid. The product was purified by high pressure liquid chromatography (silica gel 100% ethyl acetate) followed by recrystallization from isopropyl alcohol to yield 2.75 g (39%) of 4-[5-fluoro-1-[4-(trifluoromethyl)phenyl]-1H-indazol-3-yl]piperidine-1-carboxamide, mp 172°-174°.

Workup

  1. temperatureThe mixture was warmed on a steam bath until gas
  2. extractionthe product extracted (dichloromethane)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customto yield 6.9 of an oil
  6. customThe oil was triturated with water
  7. customto produce 6.9 of a solid
  8. customThe product was purified by high pressure liquid chromatography (silica gel 100% ethyl acetate)
  9. customfollowed by recrystallization from isopropyl alcohol

Sources & evidence

ORD record
ord-592046063444441a8171f455bd3702a9
Source dataset
uspto-grants-1987_12
Patent number
US04710573

Reaction notes

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