Hydrochloric Acid → HCID 57906534, compound

HRID 420529Notes

Reaction equation

[NH2:1][C:2]1[C:3]2[N:4]([C:18]([N:21]3[CH2:26][CH2:25][O:24][CH2:23][CH2:22]3)=[CH:19][N:20]=2)[CH:5]=[C:6]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=2[Cl:17])[C:7]=1[C:8]#[N:9].B.C1COCC1.Cl.CO>C1COCC1.O1CCOCC1>[NH2:9][CH2:8][C:7]1[C:6]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=2[Cl:17])=[CH:5][N:4]2[C:18]([N:21]3[CH2:26][CH2:25][O:24][CH2:23][CH2:22]3)=[CH:19][N:20]=[C:3]2[C:2]=1[NH2:1]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 8-amino-6-(2,4-dichloro-phenyl)-3-morpholin-4-yl-imidazo[1,2-a]pyridine-7-carbonitrile (112 mg, 0.29 mmol) in THF (4 mL) was added a BH3.THF complex (1.0 M solution in THF, 1.2 mL, 1.2 mmol) followed by a 4M HCl solution in dioxane (2 drops). The reaction mixture was stirred and refluxed for 3 h, then cooled to 0° C. (ice bath) and poured into MeOH. The mixture was concentrated under vacuum, the remaining residue was dissolved in a 2M HCl solution in water, and the mixture was washed with Et2O (2×). The aqueous layer was frozen and lyophilized. The remaining residue was purified by recrystallization in a mixture of MeOH/AcOEt to yield the title compound (2HCl salt, 36 mg, 0.077 mmol, 27%). MS: 392 [M+1]+; HPLC: AtRet=1.13.

Workup

temperaturerefluxed for 3 h
concentrationThe mixture was concentrated under vacuum
dissolutionthe remaining residue was dissolved in a 2M HCl solution in water
washthe mixture was washed with Et2O (2×)
temperatureThe aqueous layer was frozen
customThe remaining residue was purified by recrystallization in a mixture of MeOH/AcOEt

Sources & evidence

ORD record: ord-fc92ef32675345cd9363ca364097e500
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08097617B2

Reaction notes

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