3-[(3S)-1-methyl-2-oxo-pyrrolidin-3-yl]oxy-N-(5-methylpyrazin-2-yl)-5-phenylmethoxy-benzamide → 3-hydroxy-5-[(3S)-1-methyl-2-oxo-pyrrolidin-3-yl]oxy-N-(5-methylpyrazin-2-yl)benzamide

HRID 600543Notes

Reaction equation

HRID 600543 reaction equation
[CH3:1][N:2]1[CH2:6][CH2:5][C@H:4]([O:7][C:8]2[CH:9]=[C:10]([CH:21]=[C:22]([O:24]CC3C=CC=CC=3)[CH:23]=2)[C:11]([NH:13][C:14]2[CH:19]=[N:18][C:17]([CH3:20])=[CH:16][N:15]=2)=[O:12])[C:3]1=[O:32]>C1COCC1.CO.[Pd]>[OH:24][C:22]1[CH:21]=[C:10]([CH:9]=[C:8]([O:7][C@H:4]2[CH2:5][CH2:6][N:2]([CH3:1])[C:3]2=[O:32])[CH:23]=1)[C:11]([NH:13][C:14]1[CH:19]=[N:18][C:17]([CH3:20])=[CH:16][N:15]=1)=[O:12]

Participants

5

Reactant 1

HCID 597611433-[(3S)-1-methyl-2-oxo-pyrrolidin-3-yl]oxy-N-(5-methylpyrazin-2-yl)-5-phenylmethoxy-benzamide2×

Product 1

HCID 597611393-hydroxy-5-[(3S)-1-methyl-2-oxo-pyrrolidin-3-yl]oxy-N-(5-methylpyrazin-2-yl)benzamideYield 109.5%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-[(3S)-1-methyl-2-oxo-pyrrolidin-3-yl]oxy-N-(5-methylpyrazin-2-yl)-5-phenylmethoxy-benzamide (Intermediate 19) (449 mg, 1.04 mmol) in THF (10 mL) and methanol (10 mL) containing 10% palladium on carbon (catalytic) was stirred under an atmosphere of hydrogen for 16 hours. The palladium on carbon was removed by filtration and the filtrate evaporated under reduced pressure to afford product (390 mg, 100%). 1HNMR δ (300 MHz, CDCl3) 2.07-2.22 (m, 1H), 2.54 (s, 3H), 2.57-2.70 (m, 1H), 2.97 (s, 3H), 3.38-3.58 (m, 3H), 4.99 (t, 1H), 6.71 (s, 1H), 6.87 (s, 1H), 6.97 (s, 1H), 8.15 (s, 1H), 8.66 (s, 1H), 9.49 (s, 1H); m/z 343 (M+H)+.

Workup

  1. customThe palladium on carbon was removed by filtration
  2. customthe filtrate evaporated under reduced pressure

Sources & evidence

ORD record
ord-a30a1ae895f9496b8fd4052ac8d19dd4
Source dataset
uspto-grants-2011_03
Patent number
US07902200B2

Reaction notes

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