HCID 117771438, compound → HCID 117771656, compound

HRID 2201547Notes

Reaction equation

HRID 2201547 reaction equation
C([O:8][C:9]1[C:10]([C:41]([NH:43][CH2:44][C:45]2[CH:50]=[CH:49][C:48]([F:51])=[CH:47][CH:46]=2)=[O:42])=[N:11][C:12]([C:15]2[C:16]([N:35]([CH3:40])[S:36]([CH3:39])(=[O:38])=[O:37])=[CH:17][C:18]3[O:22][C:21]([C:23]4[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=4)=[C:20]([C:30](=[O:33])[NH:31][CH3:32])[C:19]=3[CH:34]=2)=[CH:13][CH:14]=1)C1C=CC=CC=1>CO.[Pd]>[F:51][C:48]1[CH:47]=[CH:46][C:45]([CH2:44][NH:43][C:41](=[O:42])[C:10]2[C:9]([OH:8])=[CH:14][CH:13]=[C:12]([C:15]3[C:16]([N:35]([CH3:40])[S:36]([CH3:39])(=[O:37])=[O:38])=[CH:17][C:18]4[O:22][C:21]([C:23]5[CH:24]=[CH:25][C:26]([F:29])=[CH:27][CH:28]=5)=[C:20]([C:30](=[O:33])[NH:31][CH3:32])[C:19]=4[CH:34]=3)[N:11]=2)=[CH:50][CH:49]=1

Participants

4

Reactant 1

HCID 117771438HCID 117771438, compound

Product 1

HCID 117771656HCID 117771656, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 3-(benzyloxy)-N-(4-fluorobenzyl)-6-(2-(4-fluorophenyl)-3-(methylcarbamoyl)-6-(N-methylmethylsulfonamido)benzofuran-5-yl)picolinamide (361 mg, 0.51 mmol) in CH3OH (5 mL) was added Pd—C under Ar. The suspension was degassed under vacuum and purged with H2 several times. The mixture was stirred under H2 at RT overnight. After being filtered through celite and removal of the solvent by concentration, the residue was purified by prep-TLC (DCM:MeOH=60:1) to afford the product of N-(4-fluorobenzyl)-6-(2-(4-fluorophenyl)-3-(methylcarbamoyl)-6-(N-methylmethylsulfonamido)benzofuran-5-yl)-3-hydroxypicolinamide. (220 mg, yield: 70%). 1H-NMR (CDCl3, 400 MHz) δ 12.27 (s, 1H), 8.61˜8.64 (m, 1H), 7.91˜7.96 (m, 3H), 7.64 (d, J=8.8 Hz, 1H), 7.55 (s, 1H), 7.42 (d, J=8.4 Hz, 1H), 7.35 (dd, J=5.6, 8.4 Hz, 2H), 7.21 (t, J=8.4 Hz, 2H), 7.01 (t, J=8.4 Hz, 2H), 5.80 (d, J=3.6 Hz, 1H), 4.59 (d, J=6.4 Hz, 2H), 3.04 (s, 3H), 2.97 (d, J=5.2 Hz, 3H), 2.91 (s, 3H). MS (M+H)+: 621.

Workup

  1. customThe suspension was degassed under vacuum
  2. custompurged with H2 several times
  3. filtrationAfter being filtered through celite and removal of the solvent by concentration
  4. customthe residue was purified by prep-TLC (DCM:MeOH=60:1)

Sources & evidence

ORD record
ord-a9f1e7631aab4f94ab2a84819681d007
Source dataset
uspto-grants-2016_06
Patent number
US09364482B2

Reaction notes

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