Trifluoroacetic acid → 6-Cyclopropyl-2-phenyl-imidazo[1,2-a]pyridin-7-ylamine

HRID 908233Notes

Reaction equation

HRID 908233 reaction equation
FC(F)(F)C(O)=O.C(OC(=O)[NH:14][C:15]1[C:20]([CH:21]2[CH2:23][CH2:22]2)=[CH:19][N:18]2[CH:24]=[C:25]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[N:26]=[C:17]2[CH:16]=1)(C)(C)C>ClCCl>[CH:21]1([C:20]2[C:15]([NH2:14])=[CH:16][C:17]3[N:18]([CH:24]=[C:25]([C:27]4[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=4)[N:26]=3)[CH:19]=2)[CH2:23][CH2:22]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67041799(6-Cyclopropyl-2-phenyl-imidazo[1,2-a]pyridin-7-yl)-carbamic acid tert-butyl ester

Product 1

HCID 670417926-Cyclopropyl-2-phenyl-imidazo[1,2-a]pyridin-7-ylamineYield 61%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Trifluoroacetic acid (1.5 ml) was added to a solution of (6-cyclopropyl-2-phenyl-imidazo[1,2-a]pyridin-7-yl)-carbamic acid tert-butyl ester (470 mg, 1.35 mmol) in dichloromethane (3 ml), and the mixture was stirred at r.t. (1 h). The mixture was then taken up in dichloromethane and washed. The organic layers were dried (Na2SO4) and evaporated. The title compound (204 mg, 61%) was isolated from the residue by column chromatography (silica gel, dichloromethane:methanol=100:0-90:10). MS (m/e)=250.1 [M+H+].

Workup

  1. washwashed
  2. dry with materialThe organic layers were dried (Na2SO4)
  3. customevaporated

Sources & evidence

ORD record
ord-05dfcb4419e644e8a255d704d5149fc6
Source dataset
uspto-grants-2011_09
Patent number
US08017604B2

Reaction notes

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