Methanol → HCID 86723807, compound

HRID 577580Notes

Reaction equation

HRID 577580 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]([C:28]([NH:30][CH3:31])=[O:29])[CH: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.[CH3:35]O>[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]([C:28]([N:30]([CH3:31])[CH3:35])=[O:29])[CH:26]=[CH:27][C:20]=2[O:19][CH2:18][CH2:17]1

Participants

4

Reactant 2

HCID 887MethanolHCID 86723806HCID 86723806, compound

Product 1

HCID 86723807HCID 86723807, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A mixture of 4-{[2-(benzyloxy)-4,6-dimethylpyridin-3-yl]methyl}-N,6-dimethyl-5-oxo-2,3,4,5-tetrahydro-1,4-benzoxazepine-7-carboxamide (130 g, 0.17 g, 0.36 mmol) and Pd/C (93 mg) in MeOH (15 mL) was stirred at room temperature under an H2 balloon for 2 hours. The reaction mixture was concentrated under vacuum to give the title compound (Example 130, 130 mg, 94%) as a white solid. 1H NMR (400 MHz, chloroform-d): δ 11.34 (s, 1H), 7.18-7.16 (d, 1H), 6.88-6.86 (d, 1H), 5.97 (s, 1H), 4.90-4.86 (d, 2H), 4.12 (s, 1H), 3.93 (s, 1H), 3.53 (s, 2H), 3.13 (s, 3H), 2.85 (s, 3H), 2.36-2.35 (d, 6H), 2.27 (s, 3H); MS 256.8 [M+H].

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum

Sources & evidence

ORD record
ord-d4fc2f63bc36406490bec0cb0b93e752
Source dataset
uspto-grants-2015_05
Patent number
US09040515B2

Reaction notes

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