HCID 66658966, compound → HCID 24849785, compound

HRID 420533Notes

Reaction equation

[NH2:1][C:2]1[N:6]2[CH:7]=[C:8]([C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=3[Cl:20])[C:9]([C:11]#[N:12])=[CH:10][C:5]2=[N:4][CH:3]=1>C1COCC1>[NH2:12][CH2:11][C:9]1[C:8]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=2[Cl:20])=[CH:7][N:6]2[C:2]([NH2:1])=[CH:3][N:4]=[C:5]2[CH:10]=1

Participants

Conditions

Temperature: 40 °C

Procedure

A solution of 3-amino-6-(2,4-dichloro-phenyl)-imidazo[1,2-a]pyridine-7-carbonitrile (517 mg, 1.71 mmol) in anhydrous THF (10 mL) was cooled to 0° C. (ice bath), treated with a 1M BH3 solution in THF (8.5 mL, 8.5 mmol) and stirred at 40° C. for 1 h. The reaction mixture was cooled to 0° C. (ice bath), quenched by the cautious addition of MeOH until gas evolution ceased and concentrated to dryness. The residue was suspended into a 2M HCl solution in water, stirred at RT for 10 min and evaporated to dryness. The resulting HCl salt was suspended into a 2M NaOH solution in water then extracted with DCM and AcOEt. The combined organic fractions were dried over Na2SO41 filtered, and evaporated under vacuum to give the crude 7-aminomethyl-6-(2,4-dichloro-phenyl)-imidazo[1,2-a]pyridin-3-ylamine (277 mg). HPLC: AtRet=0.81.

Workup

temperatureThe reaction mixture was cooled to 0° C. (ice bath)
customquenched by the cautious addition of MeOH until gas evolution
concentrationconcentrated to dryness
stirringstirred at RT for 10 min
customevaporated to dryness
extractionthen extracted with DCM and AcOEt
customThe combined organic fractions were dried over Na2SO41
filtrationfiltered
customevaporated under vacuum

Sources & evidence

ORD record: ord-14e30acc88c44109ab693a6e21cfd846
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08097617B2

Reaction notes

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