Ethyl 6-(2-(bis(tert-butoxycarbonyl)-amino)thiazol-5-yl)-8-phenylimidazo[1,2-a]pyridine-2-carboxylate → Ethyl 6-(2-aminothiazol-5-yl)-8-phenylimidazo[1,2-a]pyridine-2-carboxylate

HRID 2197551Notes

Reaction equation

HRID 2197551 reaction equation
C(OC([N:8](C(OC(C)(C)C)=O)[C:9]1[S:10][C:11]([C:14]2[CH:15]=[C:16]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:17]3[N:18]([CH:20]=[C:21]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[N:22]=3)[CH:19]=2)=[CH:12][N:13]=1)=O)(C)(C)C>C(O)(C(F)(F)F)=O>[NH2:8][C:9]1[S:10][C:11]([C:14]2[CH:15]=[C:16]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:17]3[N:18]([CH:20]=[C:21]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[N:22]=3)[CH:19]=2)=[CH:12][N:13]=1

Participants

3

Reactant 1

HCID 58207967Ethyl 6-(2-(bis(tert-butoxycarbonyl)-amino)thiazol-5-yl)-8-phenylimidazo[1,2-a]pyridine-2-carboxylate

Product 1

HCID 58207980Ethyl 6-(2-aminothiazol-5-yl)-8-phenylimidazo[1,2-a]pyridine-2-carboxylateYield 38.7%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of ethyl 6-(2-(bis(tert-butoxycarbonyl)amino)thiazol-5-yl)-8-phenyl-imidazo[1,2-a]pyridine-2-carboxylate (28 mg) in 3 ml of TFA was stirred at room temperature for 2 hours. The Solvent was evaporated and the residue made basic with NH4OH/MeOH/CH2Cl2 (1:9:90) solution, and then evaporated to dryness. The residue was purified by column chromatography on silica gel using ethyl acetate as eluent to give 7 mg of Ethyl 6-(2-aminothiazol-5-yl)-8-phenylimidazo[1,2-a]pyridine-2-carboxylate as a white solid. LCMS (Conditions C): 2.53 min (RT); (M+H)+=365.28 (100%). 1H NMR, 400 MHz, DMSO: δ 8.56 (m, 2 H), 8.11 (m, 2 H), 7.81 (s, 1 H), 7.65 (s, 1H), 7.56-7.47 (m, 3 H), 7.32 (bs, 2 H), 4.33 (q, J=7.1 Hz, 2 H), 1.31 (t, J=7.0 Hz, 3 H).

Workup

  1. customThe Solvent was evaporated
  2. customevaporated to dryness
  3. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-f07f2307046140ff9fffe98e83629cf6
Source dataset
uspto-grants-2012_12
Patent number
US08338604B2

Reaction notes

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