Diisopropylamine → HCID 89052513, compound

HRID 2277428Notes

Reaction equation

HRID 2277428 reaction equation
Cl.[F:2][C:3]1[CH:28]=[CH:27][C:6]([CH2:7][N:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]([N:18]3[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]3)=[C:10]([C:24]#[N:25])[C:9]2=[O:26])=[CH:5][CH:4]=1.[C:29](Cl)(=[O:32])[CH:30]=[CH2:31].C(NC(C)C)(C)C>ClCCl>[C:29]([N:21]1[CH2:20][CH2:19][N:18]([C:11]2[C:12]3[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=3)[N:8]([CH2:7][C:6]3[CH:5]=[CH:4][C:3]([F:2])=[CH:28][CH:27]=3)[C:9](=[O:26])[C:10]=2[C:24]#[N:25])[CH2:23][CH2:22]1)(=[O:32])[CH:30]=[CH2:31]

Participants

5

Reactant 3

HCID 7912DiisopropylamineHCID 13140Acryloyl chlorideHCID 70874272HCID 70874272, compound

Product 1

HCID 89052513HCID 89052513, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
10 °C

Procedure

To a suspension of 1-(4-Fluoro-benzyl)-2-oxo-4-piperazin-1-yl-1,2-dihydro-quinoline-3-carbonitrile hydrochloride salt (1 eq, 0.150 g, 0.41 mmole) in dichloromethane at −10° C. was added acryloyl chloride (1.1 eq, 0.054 g, 0.45 mmole) followed by the addition of diisopropylamine (1.5 eq, 0.083 g, 0.62 mmole, 0.103 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-(4-Acryloyl-piperazin-1-yl)-1-(4-fluoro-benzyl)-2-oxo-1,2-dihydro-quinoline-3-carbonitrile as a yellow solid (0.043 g, 25% calc M+H 417, obs M+H 417).

Workup

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

Sources & evidence

ORD record
ord-8d693aa1450a40fe96d0b573be36c64e
Source dataset
uspto-grants-2015_09
Patent number
US09133164B2

Reaction notes

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