Diisopropylethylamine → 6-Bromo-7-methyl-8-(3-trifluoromethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine

HRID 1497747Notes

Reaction equation

[Br:1][C:2]1[C:3]([CH3:19])=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:10]=2)[C:5]([NH2:8])=[N:6][CH:7]=1.C(OC([N:25]=[C:26]=S)=O)C.Cl.NO.CC[N:33](C(C)C)C(C)C>O1CCOCC1>[Br:1][C:2]1[C:3]([CH3:19])=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:16])[F:17])[CH:10]=2)[C:5]2[N:6]([N:33]=[C:26]([NH2:25])[N:8]=2)[CH:7]=1

Participants

Conditions

Temperature: 60 °C

Procedure

5-Bromo-4-methyl-3-(3-trifluoromethyl-phenyl)-pyridin-2-ylamine (Int. 1, 12.0 g, 36.25 mmol) was stirred in dioxane (250 mL) at RT and ethoxycarbonyl isothiocyanate (4.27 mL, 36.25 mmol) was added dropwise. The reaction mixture was stirred for 18 hrs, then the solvent was evaporated in vacuo. The resultant residue was dissolved in MeOH/IMS (1:1, 460 mL) and hydroxylamine hydrochloride (12.58 g, 181 mmol) was added and the reaction mixture was heated to 60° C. DIPEA (18.6 mL, 109 mmol) was added, and the reaction mixture was heated for a further 4.5 rs before allowing to cool. The resultant precipitate was collected by filtration, washed with MeOH and dried to afford the title compound as a white solid (11.49 g).

Workup

customthe solvent was evaporated in vacuo
dissolutionThe resultant residue was dissolved in MeOH/IMS (1:1, 460 mL)
temperaturethe reaction mixture was heated for a further 4.5 rs
temperatureto cool
filtrationThe resultant precipitate was collected by filtration
washwashed with MeOH
customdried

Sources & evidence

ORD record: ord-5b2d169b69bb49e0a314189f2b5f052d
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09199984B2

Reaction notes

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