Acryloyl chloride → HCID 66559230, compound

HRID 2277436Notes

Reaction equation

Cl.[CH3:2][N:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([NH:13][CH:14]2[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)=[C:5]([C:20]#[N:21])[C:4]1=[O:22].[C:23](Cl)(=[O:26])[CH:24]=[CH2:25].CCN(C(C)C)C(C)C>ClCCl>[C:23]([N:17]1[CH2:16][CH2:15][CH:14]([NH:13][C:6]2[C:7]3[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=3)[N:3]([CH3:2])[C:4](=[O:22])[C:5]=2[C:20]#[N:21])[CH2:19][CH2:18]1)(=[O:26])[CH:24]=[CH2:25]

Participants

Conditions

Temperature: -10 °C

Procedure

To a suspension of 1-Methyl-2-oxo-4-(piperidin-4-ylamino)-1,2-dihydro-quinoline-3-carbonitrile hydrochloride salt (leg, 0.020 g, 0.07 mmole) in dichloromethane at −10° C. was added acryloyl chloride (1.1 eq, 0.007 g, 0.077 mmole) followed by the addition of N,N′-diisopropylethylamine (1.5 eq, 0.014 g, 0.011 mmole, 0.02 mL). The resulting solution stirred at −10° C. for 1 hour then warmed to RT and stirred for an additional 2 hours. The reaction was quenched into ice cooled water and extracted with ethyl acetate (25 mL×3). Combined organic phase was washed consecutively with water, brine before drying over sodium sulfate. Organic phase was evaporated and the residue was purified by flash chromatography to afford 4-(1-Acryloyl-piperidin-4-ylamino)-1-methyl-2-oxo-1,2-dihydro-quinoline-3-carbonitrile as a yellow solid (0.004 g, 32% calc M+H 337, obs M+H 337).

Workup

temperaturethen warmed to RT
stirringstirred for an additional 2 hours
customThe reaction was quenched into ice
temperaturecooled water
extractionextracted with ethyl acetate (25 mL×3)
washCombined organic phase was washed consecutively with water, brine
dry with materialbefore drying over sodium sulfate
customOrganic phase was evaporated
customthe residue was purified by flash chromatography

Sources & evidence

ORD record: ord-ff1718e4c18946d7b7f1934255e82a13
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09133164B2

Reaction notes

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