[6-(2,4-Dichloro-phenyl)-imidazo[1,2-a]pyridin-7-ylmethyl]carbamic acid tert-butyl ester → C-[6-(2,4-dichloro-phenyl)-imidazo[1,2-a]pyridin-7-yl]-methylamine

HRID 420495Notes

Reaction equation

HRID 420495 reaction equation
C(OC(=O)[NH:7][CH2:8][C:9]1[C:14]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=2[Cl:22])=[CH:13][N:12]2[CH:23]=[CH:24][N:25]=[C:11]2[CH:10]=1)(C)(C)C>C(Cl)Cl.C(O)(C(F)(F)F)=O>[Cl:22][C:16]1[CH:17]=[C:18]([Cl:21])[CH:19]=[CH:20][C:15]=1[C:14]1[C:9]([CH2:8][NH2:7])=[CH:10][C:11]2[N:12]([CH:23]=[CH:24][N:25]=2)[CH:13]=1

Participants

4

Reactant 1

HCID 57906590[6-(2,4-Dichloro-phenyl)-imidazo[1,2-a]pyridin-7-ylmethyl]carbamic acid tert-butyl ester

Product 1

HCID 24849505C-[6-(2,4-dichloro-phenyl)-imidazo[1,2-a]pyridin-7-yl]-methylamineYield 52.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of [6-(2,4-dichloro-phenyl)-imidazo[1,2-a]pyridin-7-ylmethyl]-carbamic acid tert-butyl ester (30 mg, 0.07 mmol) in DCM (2 mL) and TFA (1 mL) was stirred at RT for 30 min, then concentrated to dryness. The remaining residue was purified by reverse phase prep-HPLC (Waters system) to give the title compound (2TFA salt, 19 mg, 0.037 mmol, 52%) as a white solid. MS: 293 [M+1]+; HPLC: AtRet=0.84.

Workup

  1. concentrationconcentrated to dryness
  2. customThe remaining residue was purified by reverse phase prep-HPLC (Waters system)

Sources & evidence

ORD record
ord-d0912f7be82747908f2991f8392641b0
Source dataset
uspto-grants-2012_01
Patent number
US08097617B2

Reaction notes

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