Diisopropylethylamine → N-{[(2S)-4-(3,4-Dichlorobenzyl)morpholin-2-yl]methyl}N'-[3-(ethylsulfonyl)propyl]urea

HRID 1371451Notes

Reaction equation

Cl.[CH2:2]([S:4]([CH2:7][CH2:8][CH2:9][NH2:10])(=[O:6])=[O:5])[CH3:3].C(N(CC)C(C)C)(C)C.[Cl:20][C:21]1[CH:22]=[C:23]([CH:45]=[CH:46][C:47]=1[Cl:48])[CH2:24][N:25]1[CH2:30][CH2:29][O:28][CH:27]([CH2:31][NH:32][C:33](=O)[O:34]C2C=CC([N+]([O-])=O)=CC=2)[CH2:26]1.C=CC1C=CC=CC=1.C=CC1C=CC(C=C)=CC=1.C1C=CC(C=O)=CC=1>ClCCl>[Cl:20][C:21]1[CH:22]=[C:23]([CH:45]=[CH:46][C:47]=1[Cl:48])[CH2:24][N:25]1[CH2:30][CH2:29][O:28][C@@H:27]([CH2:31][NH:32][C:33]([NH:10][CH2:9][CH2:8][CH2:7][S:4]([CH2:2][CH3:3])(=[O:6])=[O:5])=[O:34])[CH2:26]1

Participants

Conditions

Temperature: 22 °C

Procedure

Intermediate 40 (0.0225 g) and N,N-diisopropylethylamine (0.021 ml) were added to a solution of Intermediate 10 (0.044 g) in dichloromethane (3 ml), and the mixture was shaken at 22° C. for 19 h. Formyl polystyrene scavenging resin (2.95 mmol/g, 0.02 g) was added and the mixture shaken for 2 h. The mixture was filtered, the resin washed with dichloromethane, and the filtrate applied directly to a sulphonic acid ion exchange cartridge (2 g Isolute SCX). Elution with methanol followed by 10% 0.880 ammonia in methanol gave the crude product (0.04 g). Purification by chromatography on silica gel (Varian Bond Elut 1 g cartridge), eluting with dichloromethane, ether, ethyl acetate, and acetone, gave the title compound (0.029 mg).

Workup

stirringthe mixture shaken for 2 h
filtrationThe mixture was filtered
washthe resin washed with dichloromethane
washElution with methanol
customgave the crude product (0.04 g)
customPurification by chromatography on silica gel (Varian Bond Elut 1 g cartridge)
washeluting with dichloromethane, ether, ethyl acetate, and acetone

Sources & evidence

ORD record: ord-e3ac4aed36c247bbbb40385d346c0452
Source dataset: uspto-grants-2007_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07157457B2

Reaction notes

Loading…