N-(5-methylpyrazin-2-yl)-3-[(phenylmethyl)oxy]-5-[(3S)-tetrahydrofuran-3-yloxy]benzamide → 3-Hydroxy-N-(5-methylpyrazin-2-yl)-5-[(3S)-tetrahydrofuran-3-yloxy]benzamide

HRID 548718Notes

Reaction equation

HRID 548718 reaction equation
[CH3:1][C:2]1[N:3]=[CH:4][C:5]([NH:8][C:9](=[O:30])[C:10]2[CH:15]=[C:14]([O:16][C@H:17]3[CH2:21][CH2:20][O:19][CH2:18]3)[CH:13]=[C:12]([O:22]CC3C=CC=CC=3)[CH:11]=2)=[N:6][CH:7]=1>[Pd].C(O)C.C1COCC1>[OH:22][C:12]1[CH:11]=[C:10]([CH:15]=[C:14]([O:16][C@H:17]2[CH2:21][CH2:20][O:19][CH2:18]2)[CH:13]=1)[C:9]([NH:8][C:5]1[CH:4]=[N:3][C:2]([CH3:1])=[CH:7][N:6]=1)=[O:30]

Participants

5

Reactant 1

HCID 57663209N-(5-methylpyrazin-2-yl)-3-[(phenylmethyl)oxy]-5-[(3S)-tetrahydrofuran-3-yloxy]benzamide

Product 1

HCID 576632213-Hydroxy-N-(5-methylpyrazin-2-yl)-5-[(3S)-tetrahydrofuran-3-yloxy]benzamideYield 92.5%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

10% Palladium on charcoal (500 mg) was added to a solution of N-(5-methylpyrazin-2-yl)-3-[(phenylmethyl)oxy]-5-[(3S)-tetrahydrofuran-3-yloxy]benzamide (5.0 g, 12.34 mmol) in ethanol (50 mL) and THF (100 mL) and the mixture stirred under an atmosphere of hydrogen at RT for 16 hours. The mixture was filtered through Celite®, the solvents evaporated in vacuo to a residue which was crystallised from ethyl acetate to give the desired material (3.6 g). 1H NMR δ (d6-DMSO): 2.0 (m, 1H), 2.25 (m, 1H), 2.5 (s, 3H), 3.75-3.95 (m, 4H), 5.1 (m, 1H), 6.5 (d, 1H), 7.0 (d, 1H), 7.05 (d, 1H), 8.35 (s, 1H), 9.25 (s, 1H), 9.75 (s, 1H), 10.8 (s, 1H); m/z 316 (M+H)+.

Workup

  1. filtrationThe mixture was filtered through Celite®
  2. customthe solvents evaporated in vacuo to a residue which
  3. customwas crystallised from ethyl acetate

Sources & evidence

ORD record
ord-0c8c3f75c0864b4f8d56fa702b9d586f
Source dataset
uspto-grants-2011_05
Patent number
US07943607B2

Reaction notes

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