Triethylamine → 1,5-Dimethyl-6-methylene-1,6-dihydro-pyridine-3-carboxylic acid (2-benzylamino-4-fluoro-phenyl)-amide

HRID 930524Notes

Reaction equation

HRID 930524 reaction equation
[CH3:1][N:2]1[C:7](=O)[C:6]([CH3:9])=[CH:5][C:4]([C:10]([OH:12])=O)=[CH:3]1.Cl.[CH2:14]([NH:21][C:22]1[C:23]([NH2:29])=[CH:24][CH:25]=[C:26]([F:28])[CH:27]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[CH2:30](N(CC)CC)C>C(Cl)Cl>[CH2:14]([NH:21][C:22]1[CH:27]=[C:26]([F:28])[CH:25]=[CH:24][C:23]=1[NH:29][C:10]([C:4]1[CH:5]=[C:6]([CH3:9])[C:7](=[CH2:30])[N:2]([CH3:1])[CH:3]=1)=[O:12])[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 218859251,5-Dimethyl-6-oxo-1,6-dihydropyridine-3-carboxylic acidHCID 131735150N2-benzyl-4-fluoro-benzene-1,2-diamine hydrochloride

Product 1

HCID 1317351491,5-Dimethyl-6-methylene-1,6-dihydro-pyridine-3-carboxylic acid (2-benzylamino-4-fluoro-phenyl)-amideYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 1,5-dimethyl-6-oxo-1,6-dihydro-pyridine-3-carbonyl chloride D1′ (100.000 mg; 0.598 mmol) in dry DCM (2.000 ml) is added dropwise to a solution of N2-benzyl-4-fluoro-benzene-1,2-diamine hydrochloride E-1.4 (151.180 mg; 0.598 mmol) in DCM (2.000 ml) and triethylamin (0.249 ml; 1.795 mmol). The mixture is stirred for 1 h. Precipitation occurs; the residue is filtered off and washed with DCM (2 ml). The precipitate is then dried under vacuum (Yield: 85%, 186 mg; 0.509 mmol)

Workup

  1. customPrecipitation
  2. filtrationthe residue is filtered off
  3. washwashed with DCM (2 ml)
  4. customThe precipitate is then dried under vacuum (Yield: 85%, 186 mg; 0.509 mmol)

Sources & evidence

ORD record
ord-15417d528ef7415b89d80b052d2f3ace
Source dataset
uspto-grants-2016_03
Patent number
US09296748B2

Reaction notes

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