Water → HCID 59485785, compound

HRID 1972290Notes

Reaction equation

HRID 1972290 reaction equation
Cl[CH2:2][CH2:3][CH2:4][S:5]([N:8]([CH2:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=1)[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=1)(=[O:7])=[O:6].[Cl:27][C:28]1[CH:56]=[CH:55][C:31]([O:32][C:33]2[CH:38]=[CH:37][C:36]([N:39]3[C@@H:43]([C:44]4[CH:49]=[CH:48][CH:47]=[C:46]([C:50]([F:53])([F:52])[F:51])[CH:45]=4)[CH2:42][NH:41][C:40]3=[O:54])=[CH:35][CH:34]=2)=[CH:30][CH:29]=1.C([O-])([O-])=O.[Cs+].[Cs+].O>CN(C=O)C>[Cl:27][C:28]1[CH:29]=[CH:30][C:31]([O:32][C:33]2[CH:34]=[CH:35][C:36]([N:39]3[C@@H:43]([C:44]4[CH:49]=[CH:48][CH:47]=[C:46]([C:50]([F:52])([F:51])[F:53])[CH:45]=4)[CH2:42][N:41]([CH2:2][CH2:3][CH2:4][S:5]([N:8]([CH2:9][C:10]4[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=4)[CH2:18][C:19]4[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=4)(=[O:7])=[O:6])[C:40]3=[O:54])=[CH:37][CH:38]=2)=[CH:55][CH:56]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 594857113-Chloro-N,N-bis[(4-methoxyphenyl)methyl]-1-propanesulfonamideHCID 59485924(S)-1-(4-(4-chlorophenoxy)phenyl)-5-(3-(trifluoromethyl)phenyl)imidazolidin-2-one

Product 1

HCID 59485785HCID 59485785, compoundYield 82.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 3-chloro-N,N-bis(4-methoxybenzyl)propane-1-sulfonamide (30.0 mg, 0.075 mmol) and (S)-1-(4-(4-chloro-phenoxy)-phenyl)-5-(3-(trifluoromethyl)-phenyl)-imidazolidin-2-one (20.0 mg, 0.046 mmol) in DMF (0.8 mL) is added Cs2CO3 (22 mg, 0.069 mmol) and KI (1 mg). The resulted mixture is stirred at 80° C. for 14 h and is cooled down to room temperature. The mixture is poured into water (5 mL) and extracted with EtOAc (3×3 mL). The combined organic layers are concentrated and purified by flash column chromatography to provide (S)-3-(3-(4-(4-chlorophenoxy)phenyl)-2-oxo-4-(3-(trifluoromethyl)phenyl)imidazolidin-1-yl)-N,N-bis(4-methoxybenzyl)propane-1-sulfonamide (30 mg, 82%). HPLC-MS calculated for C41H39ClF3N3O6S (M+H+) 794.2, found 794.2.

Workup

  1. temperatureis cooled down to room temperature
  2. extractionextracted with EtOAc (3×3 mL)
  3. concentrationThe combined organic layers are concentrated
  4. custompurified by flash column chromatography

Sources & evidence

ORD record
ord-ceac0bbbdd34433790e201d9022f03b2
Source dataset
uspto-grants-2013_04
Patent number
US08431607B2

Reaction notes

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