Triethylamine → 2-(3-Fluoro-4-(methylsulfonamidomethyl)phenyl)-N-((3'-methyl-5-(trifluoromethyl)biphenyl-2-yl)methyl)propanamide

HRID 1428730Notes

Reaction equation

HRID 1428730 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:14]([CH3:18])[C:15]([OH:17])=O)[CH:5]=[CH:6][C:7]=1[CH2:8][NH:9][S:10]([CH3:13])(=[O:12])=[O:11].[CH3:19][C:20]1[CH:21]=[C:22]([C:26]2[CH:31]=[C:30]([C:32]([F:35])([F:34])[F:33])[CH:29]=[CH:28][C:27]=2[CH2:36][NH2:37])[CH:23]=[CH:24][CH:25]=1.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C>C(#N)C.C(OCC)(=O)C>[F:1][C:2]1[CH:3]=[C:4]([CH:14]([CH3:18])[C:15]([NH:37][CH2:36][C:27]2[CH:28]=[CH:29][C:30]([C:32]([F:33])([F:34])[F:35])=[CH:31][C:26]=2[C:22]2[CH:23]=[CH:24][CH:25]=[C:20]([CH3:19])[CH:21]=2)=[O:17])[CH:5]=[CH:6][C:7]=1[CH2:8][NH:9][S:10]([CH3:13])(=[O:11])=[O:12]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 866793652-(3-Fluoro-4-(methylsulfonamidomethyl)phenyl)propanoic acidHCID 86680213(3'-Methyl-5-(trifluoromethyl)biphenyl-2-yl)methanamine

Product 1

HCID 715396382-(3-Fluoro-4-(methylsulfonamidomethyl)phenyl)-N-((3'-methyl-5-(trifluoromethyl)biphenyl-2-yl)methyl)propanamideYield 84%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 2-(3-fluoro-4-(methylsulfonamidomethyl)phenyl)propanoic acid (51 mg, 0.185 mmol) and (3′-methyl-5-(trifluoromethyl)biphenyl-2-yl)methanamine (60 mg, 0.222 mmol) in acetonitrile were added N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide (53 mg, 0.2775 mmol), 1-hydroxybenzotriazole (38 mg, 0.270 mmol) and triethylamine (0.06 mL, 0.4625 mmol). The reaction mixture was stirred for 15 h at room temperature. The residue dissolved in ethyl acetate and washed with water and brine. The organic layer was dried over magnesium sulfate and filtered. The filtrate removed in vacuo. The crude was purified by column chromatography. 2-(3-Fluoro-4-(methylsulfonamidomethyl)phenyl)-N-((3′-methyl-5-(trifluoromethyl)biphenyl-2-yl)methyl)propanamide (example 22) (81 mg) was obtained as 84% yield.

Workup

  1. washwashed with water and brine
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. filtrationfiltered
  4. customThe filtrate removed in vacuo
  5. customThe crude was purified by column chromatography

Sources & evidence

ORD record
ord-ee0b477a96074bda986a75a353b6e6df
Source dataset
uspto-grants-2015_01
Patent number
US08937092B2

Reaction notes

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