Aluminium lithium hydride → HCID 24957319, compound

HRID 1097780Notes

Reaction equation

HRID 1097780 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].C([O:9][C:10]([C:12]1[N:13]([CH:17]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[NH:20][C:19](=[O:27])[C:18]2([CH3:29])[CH3:28])[CH:14]=[N:15][CH:16]=1)=O)C>C1COCC1>[OH:9][CH2:10][C:12]1[N:13]([CH:17]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[NH:20][C:19](=[O:27])[C:18]2([CH3:29])[CH3:28])[CH:14]=[N:15][CH:16]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 24962821HCID 24962821, compound

Product 1

HCID 24957319HCID 24957319, compoundYield 82.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of LiAlH4 (1 M in ether, 1.98 mL, 1.98 mmol) is added dropwise to a solution of 3-(3,3-Dimethyl-2-oxo-1,2,3,4-tetrahydro-quinolin-4-yl)-3H-imidazole-4-carboxylic acid ethyl ester (621 mg, 1.98 mmol) in THF (10 mL) at −10° C. After 4 h at this temperature, the reaction is quenched by the addition of water (0.3 mL), NaOH solution (15%, 0.3 mL) and water (1 mL). The resulting mixture is filtered, and the solid is washed by ether (10 mL×3). The combined solution is concentrated under vacuum, and the residue is purified by reverse phase HPLC (5% to 40% acetonitrile/water with 0.1% NH4OH over 15 min) to give the title compound (445 mg). 1H NMR (400.3 MHz, MeOD): δ 7.43 (d, J=8.0 Hz, 1H) 7.39 (s, 1H), 7.35 (t, J=8 Hz 1H), 7.09-7.03 (m, 2H), 6.91 (s, 1H), 5.39 (s, 1H), 4.72 (d, J=8.0 Hz, 2H) 1.30 (s, 3H), 1.05 (s, 3H), 13C NMR (100.6 MHz, MeOD): δ 175.93, 138.02, 136.50, 133.43, 131.20, 130.68, 127.52, 124.80, 123.29, 117.07, 61.88, 54.40, 25.68, 19.97. HRMS: calculated for C15H17N3O2: 272.1399. Found: 272.1407.

Workup

  1. customthe reaction is quenched by the addition of water (0.3 mL), NaOH solution (15%, 0.3 mL) and water (1 mL)
  2. filtrationThe resulting mixture is filtered
  3. washthe solid is washed by ether (10 mL×3)
  4. concentrationThe combined solution is concentrated under vacuum
  5. customthe residue is purified by reverse phase HPLC (5% to 40% acetonitrile/water with 0.1% NH4OH over 15 min)

Sources & evidence

ORD record
ord-612e8b7447504bfd83442b9c8b46741d
Source dataset
uspto-grants-2012_03
Patent number
US08143278B2

Reaction notes

Loading…