Hydrochloric Acid → HCID 57906509, compound

HRID 420512Notes

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:23]#[N:24])=[C:11]([NH:18][CH2:19][CH:20]([CH3:22])[CH3:21])[C:12]2[N:13]([CH:15]=[CH:16][N:17]=2)[CH:14]=1.B.C1COCC1.Cl>C1COCC1.O1CCOCC1.CO>[NH2:24][CH2:23][C:10]1[C:9]([C:3]2[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=2[Cl:1])=[CH:14][N:13]2[CH:15]=[CH:16][N:17]=[C:12]2[C:11]=1[NH:18][CH2:19][CH:20]([CH3:22])[CH3:21]

Participants

Conditions

Temperature: 40 °C

Procedure

In a sealed flask, a solution of 6-(2,4-dichloro-phenyl)-8-isobutylamino-imidazo[1,2-a]pyridine-7-carbonitrile (19.1 mg, 0.053 mmol) in THF (0.5 mL) was cooled to 0° C. (ice bath), treated with BH3.THF complex (1.0 M solution in THF, 0.48 mL, 0.48 mmol) and heated at 40° C. After 1 h, the reaction was not complete according to HPLC. 4.0 M HCl in dioxane (2 drops) and additional BH3.THF complex (1.0 M solution in THF, 0.16 mL, 0.16 mmol) were added, then the reaction mixture was heated at 40° C. for 14 h, cooled to 0° C., and diluted in MeOH (large excess). The resulting mixture was concentrated under vacuum, and the remaining residue was dissolved in TFA. After evaporation to dryness, the remaining residue was purified by reverse phase prep-HPLC (Waters system) to give the title compound (2TFA salt, 7.6 mg, 0.013 mmol, 24%). MS: 363 [M+1]+; HPLC: AtRet=1.47.

Workup

temperaturethe reaction mixture was heated at 40° C. for 14 h
temperaturecooled to 0° C.
concentrationThe resulting mixture was concentrated under vacuum
dissolutionthe remaining residue was dissolved in TFA
customAfter evaporation to dryness
customthe remaining residue was purified by reverse phase prep-HPLC (Waters system)

Sources & evidence

ORD record: ord-b093f44e4e7741d39044f0ebf871fbac
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08097617B2

Reaction notes

Loading…