Ammonium formate → 3-[(1-Methylethyl)oxy]-5-[(4-methyl-5-oxo-2,3,4,5-tetrahydro-1,4-benzoxazepin-8-yl)oxy]-N-(1-methyl-1H-pyrazol-3-yl)benzamide

HRID 548695Notes

Reaction equation

Cl[C:2]1[C:12]2[O:11][CH2:10][CH2:9][N:8]([CH3:13])[C:7](=[O:14])[C:6]=2[CH:5]=[CH:4][C:3]=1[O:15][C:16]1[CH:17]=[C:18]([CH:28]=[C:29]([O:31][CH:32]([CH3:34])[CH3:33])[CH:30]=1)[C:19]([NH:21][C:22]1[CH:26]=[CH:25][N:24]([CH3:27])[N:23]=1)=[O:20].C([O-])=O.[NH4+]>C(O)C.[Pd]>[CH3:34][CH:32]([O:31][C:29]1[CH:28]=[C:18]([CH:17]=[C:16]([O:15][C:3]2[CH:4]=[CH:5][C:6]3[C:7](=[O:14])[N:8]([CH3:13])[CH2:9][CH2:10][O:11][C:12]=3[CH:2]=2)[CH:30]=1)[C:19]([NH:21][C:22]1[CH:26]=[CH:25][N:24]([CH3:27])[N:23]=1)=[O:20])[CH3:33]

Participants

Conditions

Temperature: 140 °C

Procedure

To a solution of 3-[(9-chloro-4-methyl-5-oxo-2,3,4,5-tetrahydro-1,4-benzoxazepin-8-yl)oxy]-5-[(1-methylethyl)oxy]-N-(1-methyl-1H-pyrazol-3-yl)benzamide (160 mg, 0.32 mmol) in ethanol (3 mL) was added ammonium formate (208 mg, 10 equivs) in one portion. The reaction was blanketed with argon and 10% Palladium on carbon (40 mg) was added. The mixture was heated to 140° C. for 10 minutes in a Smith Creator microwave. The reaction mixture was filtered through diatomaceous earth and the filter pad was washed well with ethyl acetate. The filtrate was concentrated in vacuo and the residue purified by chromatography on alumina, eluting with 50-100% ethyl acetate in hexanes, to afford the title compound as a colourless oil which foamed under high vacuum (65 mg).

Workup

additionwas added
filtrationThe reaction mixture was filtered through diatomaceous earth
washthe filter pad was washed well with ethyl acetate
concentrationThe filtrate was concentrated in vacuo
customthe residue purified by chromatography on alumina
washeluting with 50-100% ethyl acetate in hexanes

Sources & evidence

ORD record: ord-e3f4949dbd674ccca4ddcab4335ff2d2
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07943607B2

Reaction notes

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