Diisopropylethylamine → N-((3R,6S)-1-(cyclopropylmethyl)-2-oxo-6-phenylazepan-3-yl)-4-(2-oxo-1,2-dihydroquinazolin-3(4H)-yl)piperidine-1-carboxamide

HRID 1271493Notes

Reaction equation

HRID 1271493 reaction equation
C(N(C(C)C)CC)(C)C.[NH2:10][C@@H:11]1[CH2:17][CH2:16][C@@H:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:14][N:13]([CH2:24][CH:25]2[CH2:27][CH2:26]2)[C:12]1=[O:28].[O:29]=[C:30]1[N:39]([CH:40]2[CH2:45][CH2:44][N:43]([C:46](Cl)=[O:47])[CH2:42][CH2:41]2)[CH2:38][C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[NH:31]1>ClCCCl>[CH:25]1([CH2:24][N:13]2[CH2:14][C@H:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH2:16][CH2:17][C@@H:11]([NH:10][C:46]([N:43]3[CH2:44][CH2:45][CH:40]([N:39]4[CH2:38][C:37]5[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=5)[NH:31][C:30]4=[O:29])[CH2:41][CH2:42]3)=[O:47])[C:12]2=[O:28])[CH2:27][CH2:26]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 183211084-(2-oxo-1,4-dihydroquinazolin-3(2H)-yl)piperidine-1-carbonyl chlorideHCID 58844837(3R,6S)-3-amino-1-(cyclopropylmethyl)-6-phenylazepan-2-one

Product 1

HCID 11375754N-((3R,6S)-1-(cyclopropylmethyl)-2-oxo-6-phenylazepan-3-yl)-4-(2-oxo-1,2-dihydroquinazolin-3(4H)-yl)piperidine-1-carboxamideYield 13.8%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Diisopropylethylamine (0.16 mL, 0.90 mmol) was added to a solution of (3R,6S)-3-amino-1-(cyclopropylmethyl)-6-phenylazepan-2-one (116 mg, 0.45 mmol) and 4-(2-oxo-1,4-dihydroquinazolin-3(2H)-yl)piperidine-1-carbonyl chloride (132 mg, 0.45 mmol) in 1,2-dichloroethane (10 mL) and the mixture heated to reflux. After 1 h, the mixture was allowed to cool to ambient temperature and concentrated. Purification by silica gel chromatography (100% dichloromethane→5% methanol/dichloromethane) gave the title compound (32 mg). MS 516 (M+1).

Workup

  1. temperaturethe mixture heated to reflux
  2. concentrationconcentrated
  3. customPurification by silica gel chromatography (100% dichloromethane→5% methanol/dichloromethane)

Sources & evidence

ORD record
ord-eea36971c3774451bf99c3d8755ef1a9
Source dataset
uspto-grants-2007_04
Patent number
US07205292B2

Reaction notes

Loading…