4-{[2-(benzyloxy)-4,6-dimethylpyridin-3-yl]methyl}-6-methyl-7-(propan-2-yloxy)-3,4-dihydropyrido[4,3-f][1,4]oxazepin-5(2H)-one → 4-[(4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl]-6-methyl-7-(propan-2-yloxy)-3,4-dihydropyrido[4,3-f][1,4]oxazepin-5(2H)-one

HRID 577588Notes

Reaction equation

HRID 577588 reaction equation
C([O:8][C:9]1[C:14]([CH2:15][N:16]2[C:22](=[O:23])[C:21]3[C:24]([CH3:32])=[C:25]([O:28][CH:29]([CH3:31])[CH3:30])[N:26]=[CH:27][C:20]=3[O:19][CH2:18][CH2:17]2)=[C:13]([CH3:33])[CH:12]=[C:11]([CH3:34])[N:10]=1)C1C=CC=CC=1>CO.[Pd]>[CH3:33][C:13]1[CH:12]=[C:11]([CH3:34])[NH:10][C:9](=[O:8])[C:14]=1[CH2:15][N:16]1[C:22](=[O:23])[C:21]2[C:24]([CH3:32])=[C:25]([O:28][CH:29]([CH3:30])[CH3:31])[N:26]=[CH:27][C:20]=2[O:19][CH2:18][CH2:17]1

Participants

4

Reactant 1

HCID 867238144-{[2-(benzyloxy)-4,6-dimethylpyridin-3-yl]methyl}-6-methyl-7-(propan-2-yloxy)-3,4-dihydropyrido[4,3-f][1,4]oxazepin-5(2H)-one

Product 1

HCID 867238154-[(4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl]-6-methyl-7-(propan-2-yloxy)-3,4-dihydropyrido[4,3-f][1,4]oxazepin-5(2H)-oneYield 98.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 4-{[2-(benzyloxy)-4,6-dimethylpyridin-3-yl]methyl}-6-methyl-7-(propan-2-yloxy)-3,4-dihydropyrido[4,3-f][1,4]oxazepin-5(2H)-one (131 g, 140 mg, 0.30 mmol) and 10% Pd/C (80 mg) in MeOH (15 mL) was stirred under an H2 balloon for 3 hours. The reaction mixture was filtered through a pad of CELITE® and the filtrate was concentrated under vacuum to give the title compound (Example 131, 110 mg, 98%) as a white solid. 1H NMR (400 MHz, chloroform-d): δ 11.45 (s, 1H), 7.72 (s, 1H), 5.97 (s, 1H), 5.26-5.21 (m, 1H), 4.87 (s, 2H), 4.00-3.97 (t, 2H), 3.56-3.53 (t, 2H), 2.36 (s, 3H), 2.28-2.26 (d, 6H), 1.35-1.33 (d, 6H); MS 372.2 [M+H].

Workup

  1. filtrationThe reaction mixture was filtered through a pad of CELITE®
  2. concentrationthe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-0c89a3bc2b13451889c1d508cee4567e
Source dataset
uspto-grants-2015_05
Patent number
US09040515B2

Reaction notes

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