Acetic Anhydride → HCID 67812066, compound

HRID 2401401Notes

Reaction equation

[NH2:1][CH:2]1[N:8]=[C:7]([C:9]2[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[CH:11][CH:10]=2)[C:6]2[CH:17]=[CH:18][CH:19]=[CH:20][C:5]=2[C:4]2[C:21]([CH3:24])=[N:22][O:23][C:3]1=2.[C:25](OC(=O)C)(=[O:27])[CH3:26].C(N(CC)CC)C>CN(C1C=CN=CC=1)C>[C:13]([C:12]1[CH:11]=[CH:10][C:9]([C:7]2[C:6]3[CH:17]=[CH:18][CH:19]=[CH:20][C:5]=3[C:4]3[C:21]([CH3:24])=[N:22][O:23][C:3]=3[CH:2]([NH:1][C:25](=[O:27])[CH3:26])[N:8]=2)=[CH:16][CH:15]=1)#[N:14]

Participants

Conditions

Temperature: 0 °C

Procedure

To a round bottomed flask was added 4-(4-amino-1-methyl-4H-benzo[c]isoxazolo[4,5-e]azepin-6-yl)benzonitrile (69 mg, 0.22 mmol) and DMAP (2.7 mg, 0.022 mmol). The flask was purged with nitrogen, MeCN was added (5 mL), and the solution was cooled to 0° C. Acetic anhydride (49.5 μL, 0.53 mmol) and triethylamine (79 μL, 0.57 mmol) were added and the reaction was allowed to warm to ambient temperature and stirred for 2 h. The reaction was quenched with a 1:1 mixture of sat. aq. NaHCO3:brine and extracted with EtOAc. The organic layer was dried over Na2SO4, filtered, concentrated, and purified on a Biotage (isocratic elution 50% EtOAc:50% Hexanes) to provide the title compound as white solid (64 mg). LC/MS m/z 357 [M+H]+.

Workup

customThe flask was purged with nitrogen, MeCN
additionwas added (5 mL)
temperatureto warm to ambient temperature
customThe reaction was quenched with a 1:1 mixture of sat. aq. NaHCO3
extractionbrine and extracted with EtOAc
dry with materialThe organic layer was dried over Na2SO4
filtrationfiltered
concentrationconcentrated
custompurified on a Biotage (isocratic elution 50% EtOAc:50% Hexanes)

Sources & evidence

ORD record: ord-e461d17fc4e54cf6aa7de18fccfeb3d6
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08796261B2

Reaction notes

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