Chloroacetyl chloride → HCID 118251003, compound

HRID 2283461Notes

Reaction equation

[Cl:1][CH2:2][C:3](Cl)=[O:4].Cl.[NH:7]1[CH2:12][CH2:11][CH2:10][C@@H:9]([NH:13][C:14]2[C:19](=[O:20])[NH:18][CH:17]=[C:16]([C:21]3[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=3)[CH:15]=2)[CH2:8]1.C(N(CC)CC)C>ClCCl>[Cl:1][CH2:2][C:3]([N:7]1[CH2:12][CH2:11][CH2:10][C@@H:9]([NH:13][C:14]2[C:19](=[O:20])[NH:18][CH:17]=[C:16]([C:21]3[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=3)[CH:15]=2)[CH2:8]1)=[O:4]

Participants

Conditions

Temperature: 0 °C

Procedure

Chloroacetyl chloride (0.021 mL, 0.26 mmol) was added to a solution of (R)-5-(piperidin-3-ylamino)-[3,4′-bipyridin]-6(1H)-one hydrochloride (100 mg, 0.26 mmol) and triethylamine (0.17 mL, 1.2 mmol) in dichloromethane (5.0 mL) at 0° C. The solution was stirred at 0° C. for 30 min and was concentrated. The residue was diluted with water and extracted with 5% methanol in ethyl acetate. The organic layer was dried over sodium sulphate, filtered, and concentrated. The residue was purified on silica gel eluting with 10% methanol in dichloromethane to provide 20 mg of the title compound: 1H NMR (300 MHz, DMSO-d6) 11.80-11.95 (m, 1H), 8.45-8.60 (m, 2H), 7.60-7.70 (m, 2H), 7.20-7.35 (m, 1H), 6.70-6.95 (m, 1H), 5.50-5.80 (m, 1H), 4.20-4.50 m, 1H), 3.45-3.95 (m, 1H), 2.95-3.40 (m, 2H), 2.65-2.90 (m, 1H), 1.35-2.15 (m, 2H); MS (ES) m/z 347 (M+H).

Workup

concentrationwas concentrated
additionThe residue was diluted with water
extractionextracted with 5% methanol in ethyl acetate
dry with materialThe organic layer was dried over sodium sulphate
filtrationfiltered
concentrationconcentrated
customThe residue was purified on silica gel eluting with 10% methanol in dichloromethane

Sources & evidence

ORD record: ord-e95879a6009d4166bf36abe4adc1d51d
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09145393B2

Reaction notes

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