Benzylamine → [5-(2-Benzylamino-4-pyridyl)-4-(3-methylphenyl)-1,3-thiazol-2-yl]amine

HRID 1268733Notes

Reaction equation

HRID 1268733 reaction equation
F[C:2]1[CH:7]=[C:6]([C:8]2[S:12][C:11]([NH2:13])=[N:10][C:9]=2[C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([CH3:20])[CH:15]=2)[CH:5]=[CH:4][N:3]=1.[CH2:21]([NH2:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(=O)([O-])O.[Na+]>>[CH2:21]([NH:28][C:2]1[CH:7]=[C:6]([C:8]2[S:12][C:11]([NH2:13])=[N:10][C:9]=2[C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([CH3:20])[CH:15]=2)[CH:5]=[CH:4][N:3]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

4

Reactant 3

HCID 7504BenzylamineHCID 516892Sodium BicarbonateHCID 9878963[5-(2-Fluoro-4-pyridyl)-4-(3-methylphenyl)-1,3-thiazol-2-yl]amine

Product 1

HCID 21964259[5-(2-Benzylamino-4-pyridyl)-4-(3-methylphenyl)-1,3-thiazol-2-yl]amineYield 43%

Conditions

Temperature
150 °C

Procedure

A mixture of [5-(2-fluoro-4-pyridyl)-4-(3-methylphenyl)-1,3-thiazol-2-yl]amine (0.29 g, 1.0 mmol) and benzylamine (1.2 mL, 11 mmol) was stirred at 150° C. for 3 hrs. The reaction mixture was cooled to room temperature, saturated aqueous sodium hydrogen carbonate solution was added and the mixture was extracted with ethyl acetate. The extract was washed with water, dried and concentrated. The residue was purified by silica gel column chromatography (hexane-ethyl acetate=1:1) to give the title compound (0.16 g, yield 41%).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with water
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate=1:1)

Sources & evidence

ORD record
ord-e37c831fa5f741a3b982f8f5bf93c17d
Source dataset
uspto-grants-2007_04
Patent number
US07199124B2

Reaction notes

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