Water → HCID 118451579, compound

HRID 522838Notes

Reaction equation

HRID 522838 reaction equation
[CH2:1]([O:3][CH2:4][C:5]1[N:6]([CH2:44][C:45]([OH:48])([CH3:47])[CH3:46])[C:7]2[C:16]3[CH:15]=[CH:14][C:13]([C:17](N(OC)C)=[O:18])=[CH:12][C:11]=3[N:10]=[C:9]([NH:23][C:24]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:8]=2[N:43]=1)[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl-].[NH4+].O>C1COCC1.C(OCC)(=O)C>[CH2:1]([O:3][CH2:4][C:5]1[N:6]([CH2:44][C:45]([OH:48])([CH3:47])[CH3:46])[C:7]2[C:16]3[CH:15]=[CH:14][C:13]([CH:17]=[O:18])=[CH:12][C:11]=3[N:10]=[C:9]([NH:23][C:24]([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)([C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=3)[C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)[C:8]=2[N:43]=1)[CH3:2]

Participants

7

Reactant 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 21226445Aluminium lithium hydrideHCID 118451628HCID 118451628, compound

Product 1

HCID 118451579HCID 118451579, compoundYield 103.7%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2-(ethoxymethyl)-1-(2-hydroxy-2-methylpropyl)-N-methoxy-N-methyl-4-(tritylamino)-1H-imidazo[4,5-c]quinoline-7-carboxamide (520 mg, 808 μmol) in THF (7 mL) in an inert atmosphere was added with stirring at 0° C. a solution of lithium aluminum hydride in THF (1 M, 404 μl, 404 μmol). The mixture was stirred 1 h at 0° C., saturated ammonium chloride solution (10 mL) was added slowly and finally water (20 mL) and ethyl acetate (30 mL) were added. The phases were separated, the water layer was extracted with ethyl acetate (30 mL), and the organic phases were washed with water (20 mL), combined, dried with MgSO4, and concentrated in vacuo to give the title compound (0.49 g, quant.) as white foam (LC-MS (UV peak area, ESI) 83%, 585.4 (MH+)) that was used in the next step without further purification.

Workup

  1. customThe phases were separated
  2. extractionthe water layer was extracted with ethyl acetate (30 mL)
  3. washthe organic phases were washed with water (20 mL)
  4. dry with materialdried with MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a16bb69d563c4d6fab12fc1222c4cc3b
Source dataset
uspto-grants-2016_05
Patent number
US09334268B2

Reaction notes

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