Acetic Anhydride → HCID 70975474, compound

HRID 1190816Notes

Reaction equation

[NH2:1][C@@H:2]1[CH2:7][CH2:6][CH2:5][N:4]([C:8]2[CH:13]=[C:12]([CH3:14])[N:11]=[C:10]3[N:15]([CH3:28])[C:16](=[O:27])[N:17]([CH2:18][C:19]4[CH:26]=[CH:25][CH:24]=[CH:23][C:20]=4[C:21]#[N:22])[C:9]=23)[CH2:3]1.C(N(CC)CC)C.[C:36](OC(=O)C)(=[O:38])[CH3:37].C(OCC)(=O)C>ClCCl>[C:21]([C:20]1[CH:23]=[CH:24][CH:25]=[CH:26][C:19]=1[CH2:18][N:17]1[C:9]2[C:10](=[N:11][C:12]([CH3:14])=[CH:13][C:8]=2[N:4]2[CH2:5][CH2:6][CH2:7][C@@H:2]([NH:1][C:36](=[O:38])[CH3:37])[CH2:3]2)[N:15]([CH3:28])[C:16]1=[O:27])#[N:22]

Participants

Conditions

Temperature: -5 °C

Procedure

430 mg (R)-2-[[7-(3-aminopiperidin-1-yl)-3,5-dimethyl-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl]methyl]benzonitrile (1.14 mmol) was dissolved in 5 mL dichloromethane at 0° C. 0.35 mL (2.5 mmol) triethylamine and 123 mg (1.2 mmol) acetic anhydride were added dropwise. After the reaction was continued for 1 h at 0° C., ethyl acetate was added until turbidity appeared. It was cooled at −5° C., and a lot of solid was precipitated. 270 mg white powder was obtained after filtration, with a yield of 56.6%.

Workup

customa lot of solid was precipitated

Sources & evidence

ORD record: ord-aacffa477c72455c89eebf6e654b9fc8
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08680089B2

Reaction notes

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