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

HRID 2246613Notes

Reaction equation

HRID 2246613 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, compound2×

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 (Intermediate 2, 0.46 g) in a solution of hydrogen chloride in dioxan (4M, 7 ml) was stirred at room temperature. 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-b14e88cb68fc4f9daf9b5ef14642de85
Source dataset
uspto-grants-2010_03
Patent number
US07687532B2

Reaction notes

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