Dimethylcarbamoyl Chloride → HCID 10472538, compound

HRID 1437043Notes

Reaction equation

HRID 1437043 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C:9]1[CH2:14][NH:13][CH2:12][CH:11]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:10]=1.C(N(CC)CC)C.[CH3:28][N:29]([CH3:33])[C:30](Cl)=[O:31]>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C:9]1[CH2:14][N:13]([C:30]([N:29]([CH3:33])[CH3:28])=[O:31])[CH2:12][CH:11]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:10]=1

Participants

5

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 8471TriethylamineHCID 57940603HCID 57940603, compound

Product 1

HCID 10472538HCID 10472538, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-(2,5-difluorophenyl)-3-phenyl-1,2,3,6-tetrahydropyridine (1-7, 1.0 mg, 4 μmol) was dissolved in anhydrous CH2Cl2 (1.0 mL) and treated with excess triethylamine (10 μL) and dimethylcarbamoyl chloride (1.1 mg, 12 μmol). Upon completion the reaction was directly subjected to flash column chromatography (SiO2, 0-80% EtOAc-hexanes gradient) to yield 5-(2,5-difluorophenyl)-N,N-dimethyl-3-phenyl-3,6-dihydropyridine-1(2H)-carboxamide (1-8). MS 343.4 found 343.4 (M+H+) required.

Sources & evidence

ORD record
ord-71b3e47e2e974e6e88db0b01049cbbec
Source dataset
uspto-grants-2009_11
Patent number
US07622468B2

Reaction notes

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