Pyridine → HCID 22034170, compound

HRID 1792141Notes

Reaction equation

HRID 1792141 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH3:12])[C:7](=[O:13])[CH:6]=[C:5]2[C:14]([F:17])([F:16])[F:15].N1C=CC=CC=1.[CH3:24][C:25]1[CH:35]=[CH:34][C:28]([CH2:29][CH2:30][N:31]=[C:32]=[S:33])=[CH:27][CH:26]=1>CN1C(=O)CCC1>[CH3:12][N:8]1[C:9]2[C:4](=[CH:3][C:2]([NH:1][C:32]([NH:31][CH2:30][CH2:29][C:28]3[CH:27]=[CH:26][C:25]([CH3:24])=[CH:35][CH:34]=3)=[S:33])=[CH:11][CH:10]=2)[C:5]([C:14]([F:17])([F:15])[F:16])=[CH:6][C:7]1=[O:13]

Participants

5

Reactant 3

HCID 1049PyridineHCID 1394094-Methylphenethyl isothiocyanateHCID 22034191HCID 22034191, compound

Product 1

HCID 22034170HCID 22034170, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent3×

Procedure

6-Amino-1-methyl-4-trifluoromethyl-1H-quinolin-2-one (Preparation 1, 200 μL of a 0.2 M solution in NMP, 40 μmol) was treated with pyridine (20 μL of a 0.2 M solution in NMP, 4 μmol) & 4-methylphenethyl isothiocyanate (240 μL of a 0.2 M solution in NMP, 48 μmol). After 7 d, the mixture was concentrated, then the residue was washed with MeCN (2×150 μL) to give the title compound (3.3 mg, 20%): RT=1.87 min; m/z (ES+)=420.2 [M+H]+.

Workup

  1. concentrationthe mixture was concentrated
  2. washthe residue was washed with MeCN (2×150 μL)

Sources & evidence

ORD record
ord-5fba2f7f0da44f38995cecb0aa6fbeb1
Source dataset
uspto-grants-2006_07
Patent number
US07074933B2

Reaction notes

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