6-(2-(Tert-butoxycarbonyl(isopropyl)-amino)thiazol-5-yl)-8-phenylimidazo[1,2-a]pyridine-2-carboxylic acid → 6-(2-(Isopropylamino)thiazol-5-yl)-8-phenylimidazo[1,2-a]pyridine-2-carboxylic acid

HRID 1958484Notes

Reaction equation

HRID 1958484 reaction equation
C(OC([N:8]([CH:32]([CH3:34])[CH3:33])[C:9]1[S:10][C:11]([C:14]2[CH:15]=[C:16]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:17]3[N:18]([CH:20]=[C:21]([C:23]([OH:25])=[O:24])[N:22]=3)[CH:19]=2)=[CH:12][N:13]=1)=O)(C)(C)C>C(O)(C(F)(F)F)=O>[CH:32]([NH:8][C:9]1[S:10][C:11]([C:14]2[CH:15]=[C:16]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:17]3[N:18]([CH:20]=[C:21]([C:23]([OH:25])=[O:24])[N:22]=3)[CH:19]=2)=[CH:12][N:13]=1)([CH3:34])[CH3:33]

Participants

3

Reactant 1

HCID 582079096-(2-(Tert-butoxycarbonyl(isopropyl)-amino)thiazol-5-yl)-8-phenylimidazo[1,2-a]pyridine-2-carboxylic acid

Product 1

HCID 445530976-(2-(Isopropylamino)thiazol-5-yl)-8-phenylimidazo[1,2-a]pyridine-2-carboxylic acidYield 52.8%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 6-(2-(tert-butoxycarbonyl(isopropyl)-amino)thiazol-5-yl)-8-phenyl-imidazo[1,2-a]pyridine-2-carboxylic acid (100 mg, 0.2 mmol) in 3 ml of TFA was stirred at room temperature for 2 hours. The solvent was removed under vacuum and the residue purified by HPLC to give 40 mg of 6-(2-(isopropylamino)thiazol-5-yl)-8-phenylimidazo[1,2-a]pyridine-2-carboxylic acid. LCMS (Conditions C): 2.27 min (RT); (M+H)+=379.34 (100%). 1H NMR, 400 MHz, DMSO: δ 8.64 (s, 1 H), 8.52 (s, 1 H), 8.13 (d, J=7.3 Hz, 2 H), 7.83 (m, 2 H), 7.57-7.47 (m, 3 H), 3.87 (m, 1 H), 1.23 (d, J=6.5 Hz, 6 H).

Workup

  1. customThe solvent was removed under vacuum
  2. customthe residue purified by HPLC

Sources & evidence

ORD record
ord-f673bd82c0754a28ae79d65eb87da89a
Source dataset
uspto-grants-2013_04
Patent number
US08410128B2

Reaction notes

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