(R)-5-(Oxiran-2-ylmethoxy)quinoline → HCID 59885598, compound

HRID 843337Notes

Reaction equation

HRID 843337 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](=[O:33])[CH2:30][NH:31][CH3:32])[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:34]1[CH2:36][C@@H:35]1[CH2:37][O:38][C:39]1[CH:48]=[CH:47][CH:46]=[C:45]2[C:40]=1[CH:41]=[CH:42][CH:43]=[N:44]2>C(O)C>[C:14]1([CH2:13][CH2:12][CH2:11][CH:10]([NH:20][C:21]([CH:23]2[CH2:28][CH2:27][N:26]([C:29](=[O:33])[CH2:30][N:31]([CH2:36][C@@H:35]([OH:34])[CH2:37][O:38][C:39]3[CH:48]=[CH:47][CH:46]=[C:45]4[C:40]=3[CH:41]=[CH:42][CH:43]=[N:44]4)[CH3:32])[CH2:25][CH2:24]2)=[O:22])[CH2:9][CH2:8][CH2:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 11735808(R)-5-(Oxiran-2-ylmethoxy)quinolineHCID 187274601-[(N-methyl)-2-aminoacetyl]-piperidine-4-carboxylic acid [4-phenyl-1-(3-phenyl-propyl)-butyl]-amide

Product 1

HCID 59885598HCID 59885598, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-[(N-methyl)-2-aminoacetyl]-piperidine-4-carboxylic acid [4-phenyl-1-(3-phenyl-propyl)-butyl]-amide (63) (223.5 mg; 0.497 mmol]) is dissolved in ethanol (10 mL) at ambient temperature. (R)-5-Oxiranylmethoxy-quinoline (2) (100.0 mg; 0.497 mmol) is added, then the mixture is refluxed for 17.5 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 (110 mg) as a white solid. ESMS: MH+ 651.6.

Workup

  1. temperaturethe mixture is refluxed for 17.5 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-bfb74c66478f4d95a8c0e9e5fc98ca61
Source dataset
uspto-grants-2002_04
Patent number
US06376514B1

Reaction notes

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