Hydrochloric Acid → 7-Aminomethyl-6-(2,4-dichloro-phenyl)-imidazo[1,2-a]pyridin-8-ylamine

HRID 420515Notes

Reaction equation

HRID 420515 reaction equation
[NH2:1][C:2]1[C:3]2[N:4]([CH:18]=[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[CH:18]=[CH:19][N:20]=[C:3]2[C:2]=1[NH2:1]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 2723981Borane;tetrahydrofuranHCID 666590048-Amino-6-(2,4-dichloro-phenyl)-imidazo[1,2-a]pyridine-7-carbonitrile

Product 1

HCID 579064647-Aminomethyl-6-(2,4-dichloro-phenyl)-imidazo[1,2-a]pyridin-8-ylamineYield 62%

Reagents, catalysts & solvents 2

HCID 312751,4-DioxaneCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 8-amino-6-(2,4-dichloro-phenyl)-imidazo[1,2-a]pyridine-7-carbonitrile (32.5 mg, 0.11 mmol) in THF (1 mL) was added a BH3.THF complex (1.0 M solution in THF, 0.43 mL, 0.43 mmol) followed by 4 M HCl in dioxane (2 drops). The reaction mixture was stirred and refluxed for 4 h, then cooled to 0° C. (ice bath) and poured into MeOH. The mixture was concentrated under vacuum, then the remaining residue was dissolved in TFA, evaporated to dryness and purified by reverse phase prep-HPLC (Waters system) to give the title compound (2TFA salt, 35.7 mg, 0.067 mmol, 62%). MS: 307 [M+1]+; HPLC: AtRet=0.99.

Workup

  1. temperaturerefluxed for 4 h
  2. concentrationThe mixture was concentrated under vacuum
  3. dissolutionthe remaining residue was dissolved in TFA
  4. customevaporated to dryness
  5. custompurified by reverse phase prep-HPLC (Waters system)

Sources & evidence

ORD record
ord-6bf65c819b294b7d83942ed1dfc47fb3
Source dataset
uspto-grants-2012_01
Patent number
US08097617B2

Reaction notes

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