Hydrochloric Acid → N-Cyclopropyl-3-fluoro-5-(1H-indazol-5-yl)-4-methylbenzamide

HRID 1988931Notes

Reaction equation

HRID 1988931 reaction equation
[CH:1]1([NH:4][C:5]([C:7]2[CH:8]=[C:9]([F:30])[C:10]([CH3:29])=[C:11]([C:13]3[CH:14]=[C:15]4[C:19](=[CH:20][CH:21]=3)[N:18](C(OC(C)(C)C)=O)[N:17]=[CH:16]4)[CH:12]=2)=[O:6])[CH2:3][CH2:2]1.Cl>O1CCOCC1>[CH:1]1([NH:4][C:5](=[O:6])[C:7]2[CH:12]=[C:11]([C:13]3[CH:14]=[C:15]4[C:19](=[CH:20][CH:21]=3)[NH:18][N:17]=[CH:16]4)[C:10]([CH3:29])=[C:9]([F:30])[CH:8]=2)[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59127378HCID 59127378, compound

Product 1

HCID 10403067N-Cyclopropyl-3-fluoro-5-(1H-indazol-5-yl)-4-methylbenzamideYield 17.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 1,1-dimethylethyl 5-{5-[(cyclopropylamino)carbonyl]-3-fluoro-2-methylphenyl}-1H-indazole-1-carboxylate (Example 59) (0.46 g) in a solution of hydrogen chloride in dioxan (4M, 7 ml) was stirred at room temp. under nitrogen for 4.5 h. The solvent was evaporated and the residue was partitioned between dichloromethane (20 ml) and aqueous sodium hydroxide (2M, 20 ml). The organic layer was separated using a hydrophobic filter tube, the solvent was evaporated and the residue was purified on a Varian Bond-Elut SPE cartridge (silica, 10 g) eluting with chloroform:methanol (100:0 to 98:2) to give the title compound (0.06 g).

Workup

  1. customThe solvent was evaporated
  2. customthe residue was partitioned between dichloromethane (20 ml) and aqueous sodium hydroxide (2M, 20 ml)
  3. customThe organic layer was separated
  4. customthe solvent was evaporated
  5. customthe residue was purified on a Varian Bond-Elut SPE cartridge (silica, 10 g)
  6. washeluting with chloroform:methanol (100:0 to 98:2)

Sources & evidence

ORD record
ord-4a4e7dda642744afbed03239ed0464b9
Source dataset
uspto-grants-2010_01
Patent number
US07642276B2

Reaction notes

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