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

HRID 2212355Notes

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

Participants

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 hours. After the reaction mixture was cooled to room temperature, a saturated aqueous solution of sodium hydrogencarbonate (20 mL) was added, the resulting mixture was extracted with ethyl acetate and extract was washed with water. This extract was dried and concentrated. The residue was purified by silica gel column chromatography (hexane:ethyl acetate, 1:1) to obtain 0.16 g (yield 41%) of the title compound.

Workup

temperatureAfter the reaction mixture was cooled to room temperature
extractionthe resulting mixture was extracted with ethyl acetate
extractionextract
washwas washed with water
customThis extract was dried
concentrationconcentrated
customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate, 1:1)

Sources & evidence

ORD record: ord-dd04fedf5fe34e818a3742c78cabdb94
Source dataset: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07101899B1

Reaction notes

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