(R)-5-(Oxiran-2-ylmethoxy)quinoline → N-{1-[2-(R)-hydroxy-3-(quinolin-5-yloxy)-propyl]piperidine-4-carbonyl}-piperidine-2-carboxylic acid [4-phenyl-1-(3-phenyl-propyl)-butyl]amide

HRID 720914Notes

Reaction equation

HRID 720914 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH:10]([NH:20][C:21]([CH:23]2[CH2:28][CH2:27][CH2:26][CH2:25][N:24]2[C:29]([CH:31]2[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]2)=[O:30])=[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:37]1[CH2:39][C@@H:38]1[CH2:40][O:41][C:42]1[CH:51]=[CH:50][CH:49]=[C:48]2[C:43]=1[CH:44]=[CH:45][CH:46]=[N:47]2>C(O)C>[C:1]1([CH2:7][CH2:8][CH2:9][CH:10]([NH:20][C:21]([CH:23]2[CH2:28][CH2:27][CH2:26][CH2:25][N:24]2[C:29]([CH:31]2[CH2:36][CH2:35][N:34]([CH2:39][C@@H:38]([OH:37])[CH2:40][O:41][C:42]3[CH:51]=[CH:50][CH:49]=[C:48]4[C:43]=3[CH:44]=[CH:45][CH:46]=[N:47]4)[CH2:33][CH2:32]2)=[O:30])=[O:22])[CH2:11][CH2:12][CH2:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 11735808(R)-5-(Oxiran-2-ylmethoxy)quinolineHCID 187274921-(Piperidine-4-carbonyl)-piperidine-2-carboxylic acid [4-phenyl-1(3-phenyl-propyl)-butyl]-amide

Product 1

HCID 59885589N-{1-[2-(R)-hydroxy-3-(quinolin-5-yloxy)-propyl]piperidine-4-carbonyl}-piperidine-2-carboxylic acid [4-phenyl-1-(3-phenyl-propyl)-butyl]amideYield 72.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-(Piperidine-4-carbonyl)-piperidine-2-carboxylic acid [4-phenyl-1-(3-phenyl-propyl)-butyl]-amide (76) (243.4 mg; 0.497 mmol) is dissolved in ethanol (12 mL) at ambient temperature. (R)-5-Oxiranylmethoxy-quinoline (2) (100.0 mg; 0.497 mmol) is added, then the mixture is refluxed for 17 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 (50%→100% acetone in hexanes, then 5%→20% ethanol in acetone) affording the desired product (250 mg) as a white solid. ESMS:MH+ 691.6

Workup

  1. temperaturethe mixture is refluxed for 17 hours
  2. concentrationthe solution is concentrated in vacuo at 40° C
  3. customThe residue is purified via silica gel chromatography with gradient elution (50%→100% acetone in hexanes

Sources & evidence

ORD record
ord-44ebbc1f76c1440493a2b6ec934bce4c
Source dataset
uspto-grants-2006_11
Patent number
US07135483B2

Reaction notes

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