HCID 117771342, compound → HCID 117771752, compound

HRID 2201518Notes

Reaction equation

HRID 2201518 reaction equation
[CH2:1]([NH:8][C:9](=[O:50])[C:10]1[C:15]([O:16]CC2C=CC=CC=2)=[CH:14][CH:13]=[C:12]([C:24]2[C:25]([N:44]([CH3:49])[S:45]([CH3:48])(=[O:47])=[O:46])=[CH:26][C:27]3[O:31][C:30]([C:32]4[CH:37]=[CH:36][C:35]([F:38])=[CH:34][CH:33]=4)=[C:29]([C:39](=[O:42])[NH:40][CH3:41])[C:28]=3[CH:43]=2)[N:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CO.[Pd]>[CH2:1]([NH:8][C:9](=[O:50])[C:10]1[C:15]([OH:16])=[CH:14][CH:13]=[C:12]([C:24]2[C:25]([N:44]([CH3:49])[S:45]([CH3:48])(=[O:47])=[O:46])=[CH:26][C:27]3[O:31][C:30]([C:32]4[CH:37]=[CH:36][C:35]([F:38])=[CH:34][CH:33]=4)=[C:29]([C:39](=[O:42])[NH:40][CH3:41])[C:28]=3[CH:43]=2)[N:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 117771342HCID 117771342, compound

Product 1

HCID 117771752HCID 117771752, compoundYield 71.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of N-benzyl-3-(benzyloxy)-6-(2-(4-fluorophenyl)-3-(methylcarbamoyl)-6-(N-methylmethylsulfonamido)benzofuran-5-yl)picolinamide (200 mg, 0.29 mmol) and Pd/C (10 mg) in CH3OH (10 mL) was stirred at room temperature overnight under H2 atmosphere (50 psi). The mixture was filtered and the filtrate was concentrated in vacuum. The residue was purified by prep-TLC (DCM:EtOAc=5:1) to give the product of N-benzyl-6-(2-(4-fluorophenyl)-3-(methylcarbamoyl)-6-(N-methylmethylsulfonamido)benzofuran-5-yl)-3-hydroxypicolinamide (125 mg, yield: 71.8%). 1H-NMR (CDCl3, 400 MHz) δ 8.73 (br s, 1H), 7.84˜7.87 (m, 3H), 7.63 (d, J=8.4 Hz, 1H), 7.49 (s, 1H), 7.44 (d, J=8.4 Hz, 1H), 7.30˜7.36 (m, 4H), 7.26 (d, J=6.0 Hz, 1H), 7.19 (t, J=8.0 Hz, 2H), 6.39 (br s, 1H), 4.60 (d, J=4.8 Hz, 2H), 3.04 (s, 3H), 2.93 (d, J=3.2 Hz, 3H), 2.87 (s, 3H). MS (M+H)+: 603.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated in vacuum
  3. customThe residue was purified by prep-TLC (DCM:EtOAc=5:1)

Sources & evidence

ORD record
ord-ac3cabca1db14411b6fd5743e0c68096
Source dataset
uspto-grants-2016_06
Patent number
US09364482B2

Reaction notes

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