Water → HCID 58208022, compound

HRID 2197571Notes

Reaction equation

HRID 2197571 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:10]2[N:11]([CH:24]=[C:25]([C:27](OCC)=[O:28])[N:26]=2)[CH:12]=[C:13]([C:15]2[S:19][C:18]([CH2:20][CH:21]([CH3:23])[CH3:22])=[N:17][CH:16]=2)[CH:14]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+].O>C1COCC1>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:10]2[N:11]([CH:24]=[C:25]([CH2:27][OH:28])[N:26]=2)[CH:12]=[C:13]([C:15]2[S:19][C:18]([CH2:20][CH:21]([CH3:22])[CH3:23])=[N:17][CH:16]=2)[CH:14]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 58207999HCID 58207999, compound

Product 1

HCID 58208022HCID 58208022, compoundYield 9.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 8-(2,4-difluorophenyl)-6-(2-isobutylthiazol-5-yl)imidazo[1,2-a]pyridine-2-carboxylate (47.2 mg, 0.107 mmol) in THF (2 mL) was added lithium aluminum hydride powder (12.2 mg, 0.321 mmol). The mixture was stirred at room temperature overnight, then added 1N NaOH (12 mL) and water (3 mL), extracted with dichloromethane, concentrated. The residue was subjected to flash column chromatography using 80% ethyl acetate and hexane to give a white solid (3.9 mg, 9% yield). LCMS (Conditions C): Tr 2.83 min; (M+H)+=400.25 (100%), 401.36 (20%), 402.36 (10%). 1H NMR, 400 MHz, CDCl3: 8.22 (d, J=1.5 Hz, 1H), 7.81 (m, 1H), 7.76 (s, 1H), 7.58 (s, 1H), 7.39 (s, 1H), 7.00-6.88 (m, 2H), 4.78 (s, 2H), 2.84 (d, J=7.1 Hz, 2H), 2.08 (m, 1H), 0.97 (d, J=6.6 Hz, 6H).

Workup

  1. extractionextracted with dichloromethane
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-67f65e3f1476417e8b1d774e0d189421
Source dataset
uspto-grants-2012_12
Patent number
US08338604B2

Reaction notes

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