Water → HCID 68809696, compound

HRID 2217904Notes

Reaction equation

Cl[C:2]1[CH:11]=[CH:10][C:9]2[C:8]([C:12]([NH:14][CH2:15][CH:16]3[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]3)=[O:13])=[C:7]([Cl:22])[CH:6]=[CH:5][C:4]=2[N:3]=1.[NH:23]1[CH2:26][CH:25]([C:27]#[N:28])[CH2:24]1.C(=O)([O-])[O-].[K+].[K+].O>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.CN1CCCC1=O>[Cl:22][C:7]1[CH:6]=[CH:5][C:4]2[N:3]=[C:2]([N:23]3[CH2:26][CH:25]([C:27]#[N:28])[CH2:24]3)[CH:11]=[CH:10][C:9]=2[C:8]=1[C:12]([NH:14][CH2:15][CH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1)=[O:13]

Participants

Conditions

Temperature: 130 °C

Procedure

A mixture of 2,6-dichloro-N-(cyclohexylmethyl)-5-quinolinecarboxamide (example 43(a)) (0.25 g, 0.74 mmol), 3-azetidinecarbonitrile (prepared according to the method of JP 2001172257A), tetra-butylammonium bromide (0.25 g) and potassium carbonate (0.2 g) in N-methylpyrrolidinone were heated at 130° C. in a microwave for 2 hours. Water was added and the reaction mixture was extracted with dichloromethane. The organic fraction was washed with water, dried over magnesium sulfate and concentrated. The residue was purified firstly by C18 cartridge (eluting with 10 to 100% methanol in water) and then by chromatography (SiO2, ethyl acetate:methanol 100:0 to 50:50 as eluant) to give the sub-title compound as a solid (0.082 g).

Workup

customprepared
extractionthe reaction mixture was extracted with dichloromethane
washThe organic fraction was washed with water
dry with materialdried over magnesium sulfate
concentrationconcentrated
customThe residue was purified firstly by C18 cartridge (eluting with 10 to 100% methanol in water)

Sources & evidence

ORD record: ord-ae28076be8cf485197d93e904bdad3ee
Source dataset: uspto-grants-2008_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07408065B2

Reaction notes

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