Borane;tetrahydrofuran → C-[6-(2,4-Dichloro-phenyl)-3-morpholin-4-yl-[1,2,4]triazolo[4,3-a]pyridin-7-yl]-methylamine

HRID 420508Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:10]([C:24]#[N:25])=[CH:11][C:12]2[N:13]([C:15]([N:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)=[N:16][N:17]=2)[CH:14]=1.B.C1COCC1>C1COCC1.CO>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:10]([CH2:24][NH2:25])=[CH:11][C:12]2[N:13]([C:15]([N:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)=[N:16][N:17]=2)[CH:14]=1

Participants

Conditions

Temperature: 40 °C

Procedure

In a sealed flask, a solution of the crude 6-(2,4-dichloro-phenyl)-3-morpholin-4-yl-[1,2,4]triazolo[4,3-a]pyridine-7-carbonitrile in THF (1 mL) was cooled to 0° C. (ice bath) then treated with BH3.THF complex (1.0 M solution in THF, 0.73 mL, 0.73 mmol). The reaction mixture was heated at 40° C. for 1 h, cooled to RT, and diluted in MeOH (large excess). The mixture was concentrated under vacuum, and the remaining residue was suspended in 2.0 M HCl, and shaken for 15 min. After evaporation to dryness, the remaining residue was purified by reverse phase prep-HPLC (Waters system) to give the title compound (2TFA salt, 5 mg, 0.008 mmol, 5%) as a white solid. MS: 378 [M+1]+; HPLC: AtRet=1.15.

Workup

temperaturecooled to RT
concentrationThe mixture was concentrated under vacuum
customAfter evaporation to dryness
customthe remaining residue was purified by reverse phase prep-HPLC (Waters system)

Sources & evidence

ORD record: ord-1a55555412ac4d1980c58c07fea7ef50
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08097617B2

Reaction notes

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