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

HRID 393979Notes

Reaction equation

HRID 393979 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]([C:29]([CH:31]3[CH2:36][CH2:35][CH2:34][CH2:33][NH:32]3)=[O:30])[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: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][N:26]([C:29]([CH:31]3[CH2:36][CH2:35][CH2:34][CH2:33][N:32]3[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)=[O:30])[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

4

Reactant 2

HCID 11735808(R)-5-(Oxiran-2-ylmethoxy)quinolineHCID 121367461-(Piperidine-2-carbonyl)-piperidine-4-carboxylic acid [4-phenyl-1-(3-phenyl-propyl)-butyl]-amide

Product 1

HCID 10168893N-{1-[2-(R)-hydroxy-3-(quinolin-5-yloxy)-propyl]-piperidine-2-carbonyl}-piperidine-4-carboxylic acid [4-phenyl-1-(3-phenyl-propyl)-butyl]-amideYield 69.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-(Piperidine-2-carbonyl)-piperidine-4-carboxylic acid [4-phenyl-1-(3-phenyl-propyl)-butyl]-amide (6) (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 (240 mg) as a white solid. ESMS: MH+ 691.4

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-669e38a8ba0f47c989dd8ec2a37be7e2
Source dataset
uspto-grants-2004_10
Patent number
US06809093B2

Reaction notes

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