Ethanamine, 2,2,2-trifluoro- → 2-(Methylthio)-4-((2,2,2-trifluoroethyl)amino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile

HRID 1430782Notes

Reaction equation

[F:1][C:2]([F:6])([F:5])[CH2:3][NH2:4].[CH3:7][S:8][C:9]1[N:14]=[C:13](SC)[C:12]2=[N:17][CH:18]=[C:19]([C:20]#[N:21])[N:11]2[N:10]=1>CN1C(=O)CCC1.C(OCC)(=O)C>[CH3:7][S:8][C:9]1[N:14]=[C:13]([NH:4][CH2:3][C:2]([F:6])([F:5])[F:1])[C:12]2=[N:17][CH:18]=[C:19]([C:20]#[N:21])[N:11]2[N:10]=1

Participants

Conditions

Temperature: 120 °C

Procedure

(I3A): 2,2,2-trifluoroethanamine (1252 mg, 12.64 mmol) was added to a solution of 2,4-bis(methylthio)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile (I2A), 300 mg, 1.264 mmol) in NMP (3 mL) and the resulting mixture was heated at 120° C. for 5 h. The reaction mixture was diluted with ethyl acetate and washed with saturated sodium bicarbonate. The organic layer was dried over magnesium sulfate, filtered and concentrated in vacuo, the crude product was purified by flash chromatography on silica gel using an automated ISCO system (40 g column, eluting with 0-40% ethyl acetate/dichloromethane). 2-(methylthio)-4-((2,2,2-trifluoroethyl)amino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile (363 mg) was obtained as a white solid.

Workup

washwashed with saturated sodium bicarbonate
dry with materialThe organic layer was dried over magnesium sulfate
filtrationfiltered
concentrationconcentrated in vacuo
customthe crude product was purified by flash chromatography on silica gel using
washan automated ISCO system (40 g column, eluting with 0-40% ethyl acetate/dichloromethane)

Sources & evidence

ORD record: ord-6148ba69600c4643833acc3f65f77dd8
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08940736B2

Reaction notes

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