Trifluoroacetic acid → 6-(2-(isopropylamino)thiazol-5-yl)-N-methyl-8-phenylimidazo[1,2-a]pyridine-2-carboxamide

HRID 1958486Notes

Reaction equation

HRID 1958486 reaction equation
[CH:1]([N:4]([C:12]1[S:13][C:14]([C:17]2[CH:18]=[C:19]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[C:20]3[N:21]([CH:23]=[C:24]([C:26](=[O:29])[NH:27][CH3:28])[N:25]=3)[CH:22]=2)=[CH:15][N:16]=1)C(=O)OC(C)(C)C)([CH3:3])[CH3:2].C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH:1]([NH:4][C:12]1[S:13][C:14]([C:17]2[CH:18]=[C:19]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[C:20]3[N:21]([CH:23]=[C:24]([C:26]([NH:27][CH3:28])=[O:29])[N:25]=3)[CH:22]=2)=[CH:15][N:16]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58208027HCID 58208027, compound

Product 1

HCID 445530986-(2-(isopropylamino)thiazol-5-yl)-N-methyl-8-phenylimidazo[1,2-a]pyridine-2-carboxamideYield 62.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl isopropyl(5-(2-(methylcarbamoyl)-8-phenylimidazo[1,2-a]pyridin-6-yl)thiazol-2-yl)carbamate (30 mg) in methylenechloride (2 ml) was treated with TFA (4 ml) and stirred at room temperature for 2 hours. The solvent was removed under vacuum and the residue chromatographed on silica gel using ethyl acetate as eluent to give 15 mg of 6-(2-(isopropylamino)thiazol-5-yl)-N-methyl-8-phenylimidazo[1,2-a]pyridine-2-carboxamide as a tan solid. LCMS (Conditions C): 2.62 min (RT); (M+H)+=392.14 (100%). 1H NMR, 500 MHz, CDCl3/CD3OD: δ 8.20 (s, 1 H), 8.19 (d, J=1.65 Hz, 1 H), 7.89 (d, J=1.37 Hz, 1 H), 7.88 (s, 1 H), 7.42-7.53 (m, 3 H), 7.36 (d, J=1.92 Hz, 1 H), 7.34 (s, 1 H), 3.55-3.64 (m, 1 H), 1.34 (d, J=6.32 Hz, 6 H).

Workup

  1. customThe solvent was removed under vacuum
  2. customthe residue chromatographed on silica gel

Sources & evidence

ORD record
ord-47926856ca474011aeeb4b40ccce9f15
Source dataset
uspto-grants-2013_04
Patent number
US08410128B2

Reaction notes

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