4-Methoxybenzylamine → N2-(4-Methoxy-benzyl)-6-trifluoromethyl-pyridine-2,3-diamine

HRID 730841Notes

Reaction equation

[NH2:1][C:2]1[C:3](Cl)=[N:4][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:6][CH:7]=1.[CH3:13][O:14][C:15]1[CH:22]=[CH:21][C:18]([CH2:19][NH2:20])=[CH:17][CH:16]=1.C(=O)(O)[O-].[Na+]>C(O)CC(C)C.CO>[CH3:13][O:14][C:15]1[CH:22]=[CH:21][C:18]([CH2:19][NH:20][C:3]2[C:2]([NH2:1])=[CH:7][CH:6]=[C:5]([C:8]([F:11])([F:10])[F:9])[N:4]=2)=[CH:17][CH:16]=1

Participants

Conditions

Temperature: 220 °C

Procedure

A mixture of the 3-amino-2-chloro-6-(trifluoromethyl)pyridine (416 mg, 2.1 mmol, Matrix), 4-methoxy-benzylamine (294 mg, 2.1 mmol, Aldrich) and sodium bicarbonate (265 mg, 3.2 mmol) in isoamyl alcohol (0.6 mL) was heated at 220° C. in a microwave synthesizer for 30 min. The reaction mixture was then cooled to room temperature, diluted with MeOH (5 mL), filtered and the filtrate was evaporated in vacuo. The residue was purified by preparative HPLC (gradient 0.1% trifluoroacetic acid in acetonitrile) to give the title compound as a yellow oil. MS (ESI, pos. ion) m/z: 298 (M+1)

Workup

temperatureThe reaction mixture was then cooled to room temperature
filtrationfiltered
customthe filtrate was evaporated in vacuo
customThe residue was purified by preparative HPLC (gradient 0.1% trifluoroacetic acid in acetonitrile)

Sources & evidence

ORD record: ord-a9c6f196224943bcb39b798019d721b8
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07582761B2

Reaction notes

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