Hydrochloric Acid → 4-[2-ethyl-4-(3-methylphenyl)-1,3-thiazol-5-yl]pyridin-2-amine

HRID 1727356Notes

Reaction equation

C(OC([NH:8][C:9]1[CH:14]=[C:13]([C:15]2[S:19][C:18]([CH2:20][CH3:21])=[N:17][C:16]=2[C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([CH3:28])[CH:23]=2)[CH:12]=[CH:11][N:10]=1)=O)(C)(C)C.C(OC(NC1C=C(CC(C2C=CC=C(C)C=2)=O)C=CN=1)=O)(C)(C)C.Cl>C(=O)([O-])O.[Na+]>[CH2:20]([C:18]1[S:19][C:15]([C:13]2[CH:12]=[CH:11][N:10]=[C:9]([NH2:8])[CH:14]=2)=[C:16]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([CH3:28])[CH:23]=2)[N:17]=1)[CH3:21]

Participants

Conditions

Temperature: 100 °C

Procedure

To 5-[2-(tert-butoxycarbonylamino)-4-pyridyl]-2-ethyl-4-(3-methylphenyl)-1,3-thiazole (synthesized from 2-(2-tert-butoxycarbonylamino-4-pyridyl)-1-(3-methylphenyl)ethanone (35 g, 170 mmol) according to the method described in Example 3) was added 2N-hydrochloric acid (200 mL), and the mixture was stirred for 1 hour at 100° C. The reaction mixture was cooled to room temperature, then, made alkaline with a 2N aqueous sodium hydrogen carbonate solution (200 mL) and aqueous sodium hydrogen carbonate solution. The resulted mixture was extracted by ethyl acetate, and the extracts were washed with water. This extracts were dried and concentrated. The residue was purified by silica gel column chromatography (hexane-ethyl acetate=1:1) to obtain a crystal. This crystal was washed with isopropyl ether, to obtain a title compound (17 g, yield 55%).

Workup

temperatureThe reaction mixture was cooled to room temperature
extractionThe resulted mixture was extracted by ethyl acetate
washthe extracts were washed with water
customThis extracts were dried
concentrationconcentrated
customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate=1:1)
customto obtain a crystal
washThis crystal was washed with isopropyl ether

Sources & evidence

ORD record: ord-4769c473166842dcb6e84b204d7b1823
Source dataset: uspto-grants-2009_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07495018B2

Reaction notes

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