HCID 58523977, compound → HCID 44553095, compound

HRID 1958482Notes

Reaction equation

HRID 1958482 reaction equation
[OH:1][CH2:2][C:3]1[N:4]=[C:5]2[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[CH:9][C:8]([C:17]3[S:21][C:20]([N:22]([CH:30]([CH3:32])[CH3:31])C(=O)OC(C)(C)C)=[N:19][CH:18]=3)=[CH:7][N:6]2[CH:33]=1>C(O)(C(F)(F)F)=O>[CH:30]([NH:22][C:20]1[S:21][C:17]([C:8]2[CH:9]=[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:5]3[N:6]([CH:33]=[C:3]([CH2:2][OH:1])[N:4]=3)[CH:7]=2)=[CH:18][N:19]=1)([CH3:32])[CH3:31]

Participants

3

Reactant 1

HCID 58523977HCID 58523977, compound

Product 1

HCID 44553095HCID 44553095, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of tert-butyl 5-(2-(hydroxymethyl)-8-phenylimidazo[1,2-a]pyridin-6-yl)thiazol-2-yl(isopropyl)carbamate (75 mg) in 4 ml of TFA was stirred at room temperature for 2 hours. The solvent was evaporated and the residue was made basic with 1 N NaOH and extracted into CH2Cl2. The solvent was removed under vacuum and the residue purified by column chromatography on silica gel using ethyl acetate as eluent to give (6-(2-(isopropylamino)thiazol-5-yl)-8-phenylimidazo[1,2-a]pyridin-2-yl)methanol as a light yellow solid. LCMS (Conditions C): 1.82 min (RT); (M+H)+=365.31 (100%). 1H NMR, 400 MHz, CDCl3/CD3OD: δ 8.08 (d, 1 H), 7.89 (m, 2 H), 7.61-7.31 (m, 6 H), 4.74 (s, 2 H), 3.71 (m, 1 H), 1.32 (d, J=6.4 Hz, 6 H).

Workup

  1. customThe solvent was evaporated
  2. extractionextracted into CH2Cl2
  3. customThe solvent was removed under vacuum
  4. customthe residue purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-ca5b61f5ea6c4a578181b820298c8a9c
Source dataset
uspto-grants-2013_04
Patent number
US08410128B2

Reaction notes

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