Pyridine → HCID 81908379, compound

HRID 1923907Notes

Reaction equation

HRID 1923907 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:7](Cl)(=O)C(C)C.[C:13](=[O:23])([O:15]CC1CCCNC1)[NH2:14].[Li+].[OH-]>CN1C(=O)CCC1.CC#N.O.C(Cl)Cl.O>[NH:1]1[CH2:6][CH2:5][CH2:4][CH:3]([O:15][C:13](=[O:23])[NH:14][CH3:7])[CH2:2]1

Participants

9

Reactant 4

HCID 1049PyridineHCID 3939Lithium HydroxideHCID 62325Isobutyryl chlorideHCID 19082825HCID 19082825, compound

Product 1

HCID 81908379HCID 81908379, compoundYield 51%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 13387N-methyl-2-pyrrolidoneSolventHCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

Pyridine (1 mL) and isobutyryl chloride (0.421 g, 3.95 mmol) were added to (R)-tert-butyl 1-(3-amino-5-chloro-1H-pyrrolo [2, 3-1)]pyridin-4-yl)piperidin-3-yl(methyl) carbamate (0.300 g, 0.790 mmol; Example 112, Step A) in NMP (2 mL), and the reaction was stirred at room temperature for 1 hour. 3M aqueous LiOH (3 mL) was then added, and the reaction was stirred for 10 minutes. Water (10 mL) and DCM (10 mL) were then added, and the organic layer was separated, dried, filtered and concentrated. The crude residue was purified by reverse phase chromatography (Biotage SP4, C-18 12M+, 5-95% CH3CN/water) to give (R)-tert-butyl 1-(5-chloro-3-isobutyramido-1H-pyrrolo[2, 3-1)]pyridin-4-yl)piperidin-3-yl(methyl)carbamate (0.180 g, 51% yield).

Workup

  1. stirringthe reaction was stirred for 10 minutes
  2. customthe organic layer was separated
  3. customdried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude residue was purified by reverse phase chromatography (Biotage SP4

Sources & evidence

ORD record
ord-296de4787fce440da8f6a6539a793ec3
Source dataset
uspto-grants-2012_05
Patent number
US08178131B2

Reaction notes

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