1,2-Dichloroethane → N-[[2-(3-Chlorophenyl)-5-(trifluoromethyl)-2H-pyrazol-3-yl]-methyl]-2-[4-(methanesulfonamido-methyl)-phenyl]-propionamide

HRID 1842985Notes

Reaction equation

HRID 1842985 reaction equation
[CH3:1][S:2]([NH:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([CH:13]([CH3:17])[C:14]([OH:16])=O)=[CH:9][CH:8]=1)(=[O:4])=[O:3].[Cl:18][C:19]1[CH:20]=[C:21]([N:25]2[C:29]([CH2:30][NH2:31])=[CH:28][C:27]([C:32]([F:35])([F:34])[F:33])=[N:26]2)[CH:22]=[CH:23][CH:24]=1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C>C(#N)C.CCOC(C)=O>[Cl:18][C:19]1[CH:20]=[C:21]([N:25]2[C:29]([CH2:30][NH:31][C:14](=[O:16])[CH:13]([C:10]3[CH:9]=[CH:8][C:7]([CH2:6][NH:5][S:2]([CH3:1])(=[O:3])=[O:4])=[CH:12][CH:11]=3)[CH3:17])=[CH:28][C:27]([C:32]([F:33])([F:34])[F:35])=[N:26]2)[CH:22]=[CH:23][CH:24]=1

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 66644230(1-(3-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methanamineHCID 708161912-(4-(Methylsulfonamidomethyl)phenyl)propanoic acid

Product 1

HCID 70816085N-[[2-(3-Chlorophenyl)-5-(trifluoromethyl)-2H-pyrazol-3-yl]-methyl]-2-[4-(methanesulfonamido-methyl)-phenyl]-propionamideYield 84%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 2-(4-(methylsulfonamidomethyl)phenyl)propanoic acid (37 mg, 0.144 mmol) and (1-(3-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methanamine (44 mg, 0.158 mmol) in acetonitrile were added EDC (41 mg, 0.216 mmol), HOBt (29 mg, 0.216 mmol) and triethylamine (0.05 mL, 0.36 mmol). The reaction mixture was stirred for 15 h at room temperature. The residue dissolved in EtOAc and washed with water and brine. The organic layer was dried (MgSO4) and filtered. The solvent was removed in vacuo. The crude product was purified by CC. Example compound B5 (62 mg) was obtained in 84% yield.

Workup

  1. washwashed with water and brine
  2. dry with materialThe organic layer was dried (MgSO4)
  3. filtrationfiltered
  4. customThe solvent was removed in vacuo
  5. customThe crude product was purified by CC

Sources & evidence

ORD record
ord-f865e738a4d145838ed350400ebe5dc9
Source dataset
uspto-grants-2015_02
Patent number
US08946204B2

Reaction notes

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