Water → HCID 66863395, compound

HRID 1944010Notes

Reaction equation

HRID 1944010 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].C([O:9][C:10]([C:12]1[N:13]=[C:14]2[CH:19]=[C:18]([NH:20][C:21]([C:23]3[N:24]([CH2:36][C:37]4[CH:42]=[CH:41][CH:40]=[C:39]([F:43])[CH:38]=4)[C:25]4[C:30]([CH:31]=3)=[CH:29][C:28]([C:32]([F:35])([F:34])[F:33])=[CH:27][CH:26]=4)=[O:22])[CH:17]=[CH:16][N:15]2[CH:44]=1)=O)C.O.[OH-].[Na+]>C1COCC1>[OH:9][CH2:10][C:12]1[N:13]=[C:14]2[CH:19]=[C:18]([NH:20][C:21]([C:23]3[N:24]([CH2:36][C:37]4[CH:42]=[CH:41][CH:40]=[C:39]([F:43])[CH:38]=4)[C:25]4[C:30]([CH:31]=3)=[CH:29][C:28]([C:32]([F:34])([F:35])[F:33])=[CH:27][CH:26]=4)=[O:22])[CH:17]=[CH:16][N:15]2[CH:44]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 66863389HCID 66863389, compound

Product 1

HCID 66863395HCID 66863395, compoundYield 17.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-5 °C

Procedure

To 0.47 mL (0.47 mmol) of a molar solution of LiAlH4 diluted in 1 mL of anhydrous THF, cooled to −5° C., is added dropwise by syringe a suspension of 190 mg (0.36 mmol) of N-[2-(ethyloxycarbonyl)imidazo[1,2-a]pyrid-7-yl]-5-trifluoromethyl-1-[(3-fluorophenyl)-methyl]-1H-indole-2-carboxamide, prepared according to the protocol described in step 17.3, in 4 mL of anhydrous THF. After stirring for 3 hours at room temperature, the reaction medium is poured slowly into a mixture (v/v) of water and concentrated sodium hydroxide, and is then extracted with 3×100 mL of dichloromethane. The combined organic phases are dried over magnesium sulfate and then concentrated under reduced pressure. The crude reaction product obtained is purified by chromatography on a column of silica, eluting with a mixture of dichloromethane and methanol. 30 mg of the expected product are thus obtained.

Workup

  1. additionis added dropwise by syringe
  2. customprepared
  3. extractionis then extracted with 3×100 mL of dichloromethane
  4. dry with materialThe combined organic phases are dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe crude reaction product
  7. customobtained
  8. customis purified by chromatography on a column of silica
  9. washeluting with a mixture of dichloromethane and methanol

Sources & evidence

ORD record
ord-1bf235a605d84866b168064f1df9e12e
Source dataset
uspto-grants-2013_03
Patent number
US08394820B2

Reaction notes

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