Triethylamine → N-((5-tert-Butyl-3'-methylbiphenyl-2-yl)methyl)-2-(3-fluoro-4-(methylsulfonamidomethyl)phenyl)propanamide

HRID 1428729Notes

Reaction equation

HRID 1428729 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].[C:19]([C:23]1[CH:24]=[CH:25][C:26]([CH2:36][NH2:37])=[C:27]([C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([CH3:35])[CH:30]=2)[CH:28]=1)([CH3:22])([CH3:21])[CH3:20].CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C>C(#N)C.C(OCC)(=O)C>[C:19]([C:23]1[CH:24]=[CH:25][C:26]([CH2:36][NH:37][C:15](=[O:17])[CH:14]([C:4]2[CH:5]=[CH:6][C:7]([CH2:8][NH:9][S:10]([CH3:13])(=[O:11])=[O:12])=[C:2]([F:1])[CH:3]=2)[CH3:18])=[C:27]([C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([CH3:35])[CH:30]=2)[CH:28]=1)([CH3:22])([CH3:20])[CH3:21]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 866793652-(3-Fluoro-4-(methylsulfonamidomethyl)phenyl)propanoic acidHCID 86680212(5-Tert-butyl-3'-methylbiphenyl-2-yl)methanamine

Product 1

HCID 71539637N-((5-tert-Butyl-3'-methylbiphenyl-2-yl)methyl)-2-(3-fluoro-4-(methylsulfonamidomethyl)phenyl)propanamideYield 121.8%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 2-(3-fluoro-4-(methylsulfonamidomethyl)phenyl)propanoic acid (66 mg, 0.18 mmol) and (5-tert-butyl-3′-methylbiphenyl-2-yl)methanamine (113 mg, 0.119 mmol) in acetonitrile were added N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide (52 mg, 0.270 mmol), 1-hydroxybenzotriazole (36 mg, 0.27 mmol) and triethylamine (0.063 mL, 0.45 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 was removed in vacuo. The crude was purified by column chromatography. N-((5-tert-Butyl-3′-methylbiphenyl-2-yl)methyl)-2-(3-fluoro-4-(methylsulfonamidomethyl)phenyl)propanamide (example 21) (74 mg) was obtained as 81% yield.

Workup

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

Sources & evidence

ORD record
ord-1a541cfa72d940139f8a8835f3745610
Source dataset
uspto-grants-2015_01
Patent number
US08937092B2

Reaction notes

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