(R)-5-(Oxiran-2-ylmethoxy)quinoline → HCID 9808357, compound

HRID 720889Notes

Reaction equation

[NH:1]1[CH2:6][CH2:5][CH:4]([NH:7][C:8](=[O:28])[CH:9]([CH2:19][CH2:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:10][CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:3][CH2:2]1.[O:29]1[CH2:31][C@@H:30]1[CH2:32][O:33][C:34]1[CH:43]=[CH:42][CH:41]=[C:40]2[C:35]=1[CH:36]=[CH:37][CH:38]=[N:39]2>C(O)(C)C>[OH:29][CH:30]([CH2:32][O:33][C:34]1[CH:43]=[CH:42][CH:41]=[C:40]2[C:35]=1[CH:36]=[CH:37][CH:38]=[N:39]2)[CH2:31][N:1]1[CH2:6][CH2:5][CH:4]([NH:7][C:8](=[O:28])[CH:9]([CH2:19][CH2:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:10][CH2:11][CH2:12][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:3][CH2:2]1

Participants

Conditions

Temperature: 70 °C

Procedure

5-Phenyl-2-(3-phenyl-propyl)-pentanoic acid piperidin-4-ylamide (24) (100 mg; 0.264 mmol) is dissolved in isopropanol (10 mL) at ambient temperature. (R)-5-Oxiranylmethoxyquinoline (2) (53.2 mg; 0.264 mmol) is added, then the mixture is heated to 70° C. and maintained for 18 hours. After cooling to ambient temperature, the solution is concentrated in vacuo at 40° C. The residue is purified via silica gel chromatography with gradient elution (0%→25% methanol in methylene chloride) affording the desired product (117 mg) as a solid. ESMS: MH+ 580.4 (base).

Workup

temperaturemaintained for 18 hours
temperatureAfter cooling to ambient temperature
concentrationthe solution is concentrated in vacuo at 40° C
customThe residue is purified via silica gel chromatography with gradient elution (0%→25% methanol in methylene chloride)

Sources & evidence

ORD record: ord-6b60912410fe49b19065155b7e306c3a
Source dataset: uspto-grants-2006_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07135483B2

Reaction notes

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