Diisopropylamine → HCID 89096175, compound

HRID 2277435Notes

Reaction equation

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

Participants

Conditions

Temperature: -10 °C

Procedure

To a suspension of 4-(Azetidin-3-ylamino)-1-(2-ethoxy-ethyl)-2-oxo-1,2-dihydro-quinoline-3-carbonitrile hydrochloride salt (1 eq, 0.050 g, 0.16 mmole) in dichloromethane at −10° C. was added acryloyl chloride (1.1 eq, 0.005 g, 0.055 mmole) followed by the addition of diisopropylamine (1.5 eq, 0.031 g, 0.075 mmole, 0.05mL). 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-azetidin-3-ylamino)-1-(2-ethoxy-ethyl)-2-oxo-1,2-dihydro-quinoline-3-carbonitrile as a yellow solid (0.008 g, 28% calc M+H 367, obs M+H 367).

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
customevaporated
customthe residue was purified by flash chromatography

Sources & evidence

ORD record: ord-51402bfd66aa419b815651f2b9706c06
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09133164B2

Reaction notes

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