Water → HCID 67277950, compound

HRID 1696256Notes

Reaction equation

HRID 1696256 reaction equation
[CH3:1][C@@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@@H:3]1[NH:8][C:9]1[C:14]([C:15](OCC)=[O:16])=[CH:13][N:12]=[C:11]2[NH:20][CH:21]=[CH:22][C:10]=12.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[CH3:1][C@@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@@H:3]1[NH:8][C:9]1[C:14]([CH2:15][OH:16])=[CH:13][N:12]=[C:11]2[NH:20][CH:21]=[CH:22][C:10]=12

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 67278098HCID 67278098, compound

Product 1

HCID 67277950HCID 67277950, compoundYield 36.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 4-{[(1S,2R)-2-methylcyclohexyl]amino}-1H-pyrrolo[2,3-b]pyridine-5-carboxylate (50 mg) in tetrahydrofuran (1 mL) was added lithium aluminum hydride (21 mg) at 4° C. The reaction mixture was stirred at the same temperature for an hour, at ambient temperature for an hour, and at 60° C. for 2 hours. After cooled to ambient temperature, to the mixture was added water (0.021 ml), 15% NaOH solution (0.021 ml), water (0.063 ml) one after another. The precipitate was filtered through a celite pad. The filtrate was concentrated in vacuo. The residue was purified by preparative thin layer chromatography on silica gel eluting with chloroform:methanol=8:1 to give (4-{[(1S,2R)-2-methylcyclohexyl]amino}-1H-pyrrolo[2,3-b]pyridin-5-yl)methanol (15.6 mg) as a white powder.

Workup

  1. temperatureAfter cooled to ambient temperature, to the mixture
  2. filtrationThe precipitate was filtered through a celite pad
  3. concentrationThe filtrate was concentrated in vacuo
  4. customThe residue was purified by preparative thin layer chromatography on silica gel eluting with chloroform

Sources & evidence

ORD record
ord-17c85c7170dc48909c8c5bd88e87c9af
Source dataset
uspto-grants-2012_04
Patent number
US08163767B2

Reaction notes

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