N-{1-benzyl-3-[4-(benzyloxy)benzyl]-2-oxoazepan-3-yl}-4-(2-oxo-1,4-dihydroquinazolin-3(2H)-yl)piperidine-1-carboxamide → N-[1-Benzyl-3-(4-hydroxybenzyl)-2-oxoazepan-3-yl]-4-(2-oxo-1,4-dihydroquinazolin-3(2H)-yl)piperidine-1-carboxamide

HRID 1271502Notes

Reaction equation

HRID 1271502 reaction equation
[CH2:1]([N:8]1[CH2:14][CH2:13][CH2:12][CH2:11][C:10]([NH:30][C:31]([N:33]2[CH2:38][CH2:37][CH:36]([N:39]3[CH2:48][C:47]4[C:42](=[CH:43][CH:44]=[CH:45][CH:46]=4)[NH:41][C:40]3=[O:49])[CH2:35][CH2:34]2)=[O:32])([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([O:22]CC3C=CC=CC=3)=[CH:18][CH:17]=2)[C:9]1=[O:50])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>[Pd].C(O)C>[CH2:1]([N:8]1[CH2:14][CH2:13][CH2:12][CH2:11][C:10]([NH:30][C:31]([N:33]2[CH2:34][CH2:35][CH:36]([N:39]3[CH2:48][C:47]4[C:42](=[CH:43][CH:44]=[CH:45][CH:46]=4)[NH:41][C:40]3=[O:49])[CH2:37][CH2:38]2)=[O:32])([CH2:15][C:16]2[CH:17]=[CH:18][C:19]([OH:22])=[CH:20][CH:21]=2)[C:9]1=[O:50])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 18451933N-{1-benzyl-3-[4-(benzyloxy)benzyl]-2-oxoazepan-3-yl}-4-(2-oxo-1,4-dihydroquinazolin-3(2H)-yl)piperidine-1-carboxamide

Product 1

HCID 11433195N-[1-Benzyl-3-(4-hydroxybenzyl)-2-oxoazepan-3-yl]-4-(2-oxo-1,4-dihydroquinazolin-3(2H)-yl)piperidine-1-carboxamideYield 73.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

10% Palladium on carbon (23 mg) was added to a solution N-{1-benzyl-3-[4-(benzyloxy)benzyl]-2-oxoazepan-3-yl}-4-(2-oxo-1,4-dihydroquinazolin-3 (2H)-yl)piperidine-1-carboxamide (67 mg, 0.100 mmol) in ethanol (5 mL). The reaction vessel was evacuated and back-filled with nitrogen (3×), then back-filled with hydrogen (1 atm). After 32 h, the mixture was filtered and concentrated. Purification by silica gel chromatography (1% methanol/dichloromethane→10% methanol/dichloromethane) gave the title compound (43 mg). MS 582 (M+1).

Workup

  1. customThe reaction vessel was evacuated
  2. additionback-filled with nitrogen (3×)
  3. additionback-filled with hydrogen (1 atm)
  4. filtrationthe mixture was filtered
  5. concentrationconcentrated
  6. customPurification by silica gel chromatography (1% methanol/dichloromethane→10% methanol/dichloromethane)

Sources & evidence

ORD record
ord-57e0bf4c2b7243f694e37ddb79b30148
Source dataset
uspto-grants-2007_04
Patent number
US07205292B2

Reaction notes

Loading…