Water → HCID 68810659, compound

HRID 2217799Notes

Reaction equation

Cl[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([Cl:22])[C:8]=2[NH:12][C:13](=[O:21])[CH2:14][CH:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)[N:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:29][C:30]([O:33][C:34](=[O:39])[CH2:35][CH2:36][CH2:37][NH2:38])([CH3:32])[CH3:31].O>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.CN1CCCC1=O>[Cl:22][C:7]1[C:8]([NH:12][C:13](=[O:21])[CH2:14][CH:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)=[C:9]2[C:4](=[CH:5][CH:6]=1)[N:3]=[C:2]([NH:38][CH2:37][CH2:36][CH2:35][C:34]([O:33][C:30]([CH3:32])([CH3:31])[CH3:29])=[O:39])[CH:11]=[CH:10]2

Participants

Conditions

Temperature: 130 °C

Procedure

To a stirred solution of N-(2,6-dichloro-5-quinolinyl)-cyclohexaneacetamide (Example 1 (a)) (200 mg), potassium carbonate (410 mg) and tetrabutylammonium bromide (2 mg) in N-methylpyrrolidinone (5 mL) was added 4-amino-butanoic acid 1,1-dimethylethyl ester (1 g). The mixture was heated at 130° C. for 72 hours after which it was cooled and poured into water. The mixture was extracted with dichloromethane (3×20 mL) and the combined extracts dried, filtered and evaporated. Purification (SiO2, ethyl acetate:isohexane 3:7 as eluant) gave the sub-title compound (200 mg).

Workup

temperaturewas cooled
extractionThe mixture was extracted with dichloromethane (3×20 mL)
customthe combined extracts dried
filtrationfiltered
customevaporated
customPurification (SiO2, ethyl acetate:isohexane 3:7 as eluant)

Sources & evidence

ORD record: ord-db942da25ebb428cab7a56440e75832f
Source dataset: uspto-grants-2008_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07408065B2

Reaction notes

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