(R)-5-(Oxiran-2-ylmethoxy)quinoline → HCID 86585548, compound

HRID 720899Notes

Reaction equation

[C:1]1([CH2:7][CH2:8][CH2:9][CH:10]([NH:20][C:21]([CH:23]2[CH2:28][CH2:27][N:26]([CH3:29])[CH2:25][CH2:24]2)=[O:22])[CH2:11][CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[O:30]1[CH2:32][C@@H:31]1[CH2:33][O:34][C:35]1[CH:44]=[CH:43][CH:42]=[C:41]2[C:36]=1[CH:37]=[CH:38][CH:39]=[N:40]2>C(O)(C)C>[C:1]1([CH2:7][CH2:8][CH2:9][CH:10]([NH:20][C:21]([CH:23]2[CH2:28][CH2:27][N:26]([CH2:29][CH2:32][C@@H:31]([OH:30])[CH2:33][O:34][C:35]3[CH:44]=[CH:43][CH:42]=[C:41]4[C:36]=3[CH:37]=[CH:38][CH:39]=[N:40]4)[CH2:25][CH2:24]2)=[O:22])[CH2:11][CH2:12][CH2:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

Conditions

Temperature: 70 °C

Procedure

Methylpiperidine-4-carboxylic acid [4-phenyl-1-(3-phenyl-propyl)-butyl]-amide (57) (150 mg; 0.382 mmol) is dissolved in isopropanol (10 mL) at ambient temperature. (R)-5-Oxiranylmethoxy-quinoline (2) (77.5 mg; 0.382 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 (187.4 mg) as a solid foam. ESMS:MH+ 594.4 (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-089b47c33a9d41348e11ab939d8cafe3
Source dataset: uspto-grants-2006_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07135483B2

Reaction notes

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