1,2-Dichloroethane → HCID 178427617, compound

HRID 1797009Notes

Reaction equation

HRID 1797009 reaction equation
[F:1][C:2]([F:24])([F:23])[C:3]1[CH:4]=[C:5]([C:9]2[N:10]=[C:11]([C@H:14]3[CH2:19][CH2:18][C@H:17]([C:20](O)=[O:21])[CH2:16][CH2:15]3)[NH:12][CH:13]=2)[CH:6]=[CH:7][CH:8]=1.[CH3:25][C:26]1[CH:31]=[CH:30][C:29]([S:32]([NH2:35])(=[O:34])=[O:33])=[CH:28][CH:27]=1.C(Cl)CCl>CN(C1C=CN=CC=1)C.ClCCl>[CH3:25][C:26]1[CH:27]=[CH:28][C:29]([S:32]([NH:35][C:20]([C@H:17]2[CH2:16][CH2:15][C@H:14]([C:11]3[NH:12][CH:13]=[C:9]([C:5]4[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:24])([F:23])[F:1])[CH:4]=4)[N:10]=3)[CH2:19][CH2:18]2)=[O:21])(=[O:34])=[O:33])=[CH:30][CH:31]=1

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 6269P-ToluenesulfonamideHCID 178525698HCID 178525698, compound

Product 1

HCID 178427617HCID 178427617, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To an ice-water cooled mixture of trans-4-{4-[3-(trifluoromethyl)phenyl]imidazol-2-yl}cyclohexanecarboxylic acid (1.48 mmol), 4-methylbenzenesulfonamide (1.48 mmol), and DMAP (1.48 mmol) in dichloromethane (10 mL) under nitrogen, EDC (1.48 mmol) was added. The mixture was stirred at room temperature overnight, concentrated and chromatographed on silica gel (19:1 EtOAc-MeOH eluent) to give trans-N-[(4-methylphenyl)sulfonyl](4-{4-[3-(trifluoromethyl)phenyl]-imidazol-2-yl}cyclohexyl)carboxamide.

Workup

  1. concentrationconcentrated
  2. customchromatographed on silica gel (19:1 EtOAc-MeOH eluent)

Sources & evidence

ORD record
ord-6dedc0391ba74b9cac004d5bf1e8141e
Source dataset
uspto-grants-2006_04
Patent number
US07034034B2

Reaction notes

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