Water → HCID 81908379, compound

HRID 1923906Notes

Reaction equation

HRID 1923906 reaction equation
NC1C2C(=NC=C(Cl)C=2N2CCC[C@@H:13]([N:17](C)[C:18](=O)[O:19]C(C)(C)C)C2)NC=1.C(Cl)(=O)CC.[Li+].[OH-].O.[CH3:35][N:36]1[C:40](=[O:41])[CH2:39][CH2:38][CH2:37]1>N1C=CC=CC=1.CC#N.O.C(Cl)Cl>[NH:36]1[CH2:37][CH2:38][CH2:39][CH:40]([O:41][C:18](=[O:19])[NH:17][CH3:13])[CH2:35]1

Participants

9

Reactant 5

HCID 962WaterHCID 3939Lithium HydroxideHCID 13387N-methyl-2-pyrrolidoneHCID 62324Propionyl chlorideHCID 67081885HCID 67081885, compound

Product 1

HCID 81908379HCID 81908379, compoundYield 46%

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 6344DichloromethaneSolventHCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

(R)-tert-Butyl 1-(3-amino-5-chloro-1H-pyrrolo[2,3-b]pyridin-4-yl)piperidin-3-yl(methyl)carbamate (0.300 g, 0.790 mmol; Example 112, Step A) in NMP (2 mL), pyridine (1 mL) and propionyl chloride (0.365 g, 3.95 mmol) were 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 fraction was separated, dried, filtered, and concentrated. The crude residue was purified by reverse phase chromatography (Biotage SP4, C-18 25M+, 0-95% CH3CN/water) to give (R)-tert-butyl 1-(5-chloro-3-propionamido-1H-pyrrolo[2, 3-1)]pyridin-4-yl)piperidin-3-yl(methyl)carbamate (0.160 g, 46% yield).

Workup

  1. customthe organic fraction was separated
  2. customdried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude residue was purified by reverse phase chromatography (Biotage SP4

Sources & evidence

ORD record
ord-07a6c4b088fd47eb88b3d3a397fd1edf
Source dataset
uspto-grants-2012_05
Patent number
US08178131B2

Reaction notes

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