Triethylamine → HCID 71539639, compound

HRID 1428731Notes

Reaction equation

HRID 1428731 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[N:28]=[C:27]([C:29]2[CH:30]=[C:31]([CH3:35])[CH:32]=[CH:33][CH:34]=2)[C:26]([CH2:36][NH2:37])=[CH:25][CH:24]=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[N:28]=[C:27]([C:29]2[CH:30]=[C:31]([CH3:35])[CH:32]=[CH:33][CH:34]=2)[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])=[CH:25][CH:24]=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 86680214HCID 86680214, compound

Product 1

HCID 71539639HCID 71539639, compoundYield 80.3%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 2-(3-fluoro-4-(methylsulfonamidomethyl)phenyl)propanoic acid (82 mg, 0.297 mmol) and (6-tert-butyl-2-m-tolylpyridin-3-yl)methanamine (76 mg, 0.297 mmol) in acetonitrile were added N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide (85 mg, 0.445 mmol), 1-hydroxybenzotriazole (60 mg, 0.445 mmol) and triethylamine (0.1 mL, 0.742 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. N-((6-tert-Butyl-2-m-tolylpyridin-3-yl)methyl)-2-(3-fluoro-4-(methylsulfonamidomethyl)phenyl)propanamide (example 23) (122 mg) was obtained as 80% 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-c4650a74e8964d5e8c3b72a5cb7f64ce
Source dataset
uspto-grants-2015_01
Patent number
US08937092B2

Reaction notes

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