HCID 59408770, compound → HCID 59408767, compound

HRID 1188134Notes

Reaction equation

HRID 1188134 reaction equation
Br[C:2]1[N:7]=[C:6]([NH:8][C:9]([C:11]2[CH:15]=[C:14]([C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)[N:13]([CH:23]3[CH2:28][CH2:27][CH2:26][CH2:25][O:24]3)[N:12]=2)=[O:10])[CH:5]=[CH:4][CH:3]=1>C(N)C1C=CC=CC=1>[CH2:14]([NH:13][C:2]1[N:7]=[C:6]([NH:8][C:9]([C:11]2[CH:15]=[C:14]([C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)[N:13]([CH:23]3[CH2:28][CH2:27][CH2:26][CH2:25][O:24]3)[N:12]=2)=[O:10])[CH:5]=[CH:4][CH:3]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

3

Reactant 1

HCID 59408770HCID 59408770, compound

Product 1

HCID 59408767HCID 59408767, compoundYield 96.4%

Reagents, catalysts & solvents 1

HCID 7504BenzylamineSolvent

Conditions

Temperature
130 °C

Procedure

The 6-bromo-N-(5-(4-fluorophenyl)-1H-pyrazol-3-yl) picolinamide 3 (307 mg, 0.88 mmol) was dissolved in neat benzylamine (3 mL) without further characterization. The reaction mixture was heated at 130° C. for 24 hrs. Then the solvent was evaporated and the residue was purified on silica gel (EtOAc: pet-ether, 1:4) to give 6-(benzylamino)-N-(5-(thiophen-2-yl)-1H-pyrazol-3-yl)picolinamide 4 as a sticky solid (200 mg, 58%).

Workup

  1. customThen the solvent was evaporated
  2. customthe residue was purified on silica gel (EtOAc: pet-ether, 1:4)

Sources & evidence

ORD record
ord-d5e0ca1c7d2343b298121a48513145f0
Source dataset
uspto-grants-2014_03
Patent number
US08673940B2

Reaction notes

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