Water → 3-[3-(3,3-Diphenylpropyl)-3-(2-morpholin-4-ylethyl)ureido]thiobenzamide

HRID 254264

Reaction equation

[C:1]([C:3]1[CH:4]=[C:5]([NH:9][C:10](=[O:35])[N:11]([CH2:20][CH2:21][CH:22]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:12][CH2:13][N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[CH:6]=[CH:7][CH:8]=1)#[N:2].C([S:38]P([O-])(OCC)=S)C.O>C1COCC1>[C:29]1([CH:22]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH2:21][CH2:20][N:11]([CH2:12][CH2:13][N:14]2[CH2:15][CH2:16][O:17][CH2:18][CH2:19]2)[C:10](=[O:35])[NH:9][C:5]2[CH:4]=[C:3]([CH:8]=[CH:7][CH:6]=2)[C:1]([NH2:2])=[S:38])[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

Conditions

Temperature: 40 °C

Procedure

70 mg (0.15 mmol, 1 eq.) of 3-(3-cyanophenyl)-1-(3,3-diphenylpropyl)-1-(2-morpholin-4-ylethyl)urea (obtained in Example 19) are dissolved in 0.5 mL of THF under argon. 142 μL (0.90 mmol, 6 eq.) of diethyldithiophosphate and 50 μL (0.01 mmol, 0.1 eq.) of water are added. The mixture is stirred for 27 hours at 40° C. Water is added to the medium and the aqueous phase is extracted with dichloromethane, washed twice with water then brine, dried over MgSO4, filtered and concentrated. The oil obtained is subjected to chromatography over silica gel (eluent: 97/3 dichloromethane/methanol) in order to obtain the expected product in the form of a yellow powder (55 mg, yield=73%).

Workup

extractionthe aqueous phase is extracted with dichloromethane
washwashed twice with water
dry with materialbrine, dried over MgSO4
filtrationfiltered
concentrationconcentrated
customThe oil obtained

Sources & evidence

ORD record: ord-34a646655879462d8d9a6928ed341f88
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07875609B2

Linked notes

Loading…