Water → HCID 58208022, compound

HRID 1958498Notes

Reaction equation

HRID 1958498 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-47c15893823244b8a35f3179b9f5f587
Source dataset
uspto-grants-2013_04
Patent number
US08410128B2

Reaction notes

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