Pyridine → HCID 67082125, compound

HRID 408382Notes

Reaction equation

HRID 408382 reaction equation
N1C=CC=CC=1.[CH:7]1([C:10](Cl)=[O:11])[CH2:9][CH2:8]1.[NH2:13][C:14]1[C:22]2[C:17](=[N:18][CH:19]=[C:20]([Cl:38])[C:21]=2[N:23]2[CH2:28][CH2:27][CH2:26][C@@H:25]([N:29]([CH3:37])[C:30](=[O:36])[O:31][C:32]([CH3:35])([CH3:34])[CH3:33])[CH2:24]2)[NH:16][CH:15]=1.[Li+].[OH-]>CN1C(=O)CCC1.CC#N.O.C(Cl)Cl.O>[Cl:38][C:20]1[C:21]([N:23]2[CH2:28][CH2:27][CH2:26][C@@H:25]([N:29]([CH3:37])[C:30](=[O:36])[O:31][C:32]([CH3:33])([CH3:34])[CH3:35])[CH2:24]2)=[C:22]2[C:14]([NH:13][C:10]([CH:7]3[CH2:9][CH2:8]3)=[O:11])=[CH:15][NH:16][C:17]2=[N:18][CH:19]=1

Participants

9

Reactant 4

HCID 1049PyridineHCID 3939Lithium HydroxideHCID 77637Cyclopropanecarbonyl chlorideHCID 67081885HCID 67081885, compound

Product 1

HCID 67082125HCID 67082125, compoundYield 48%

Reagents, catalysts & solvents 4

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

Procedure

Pyridine (1 mL) and cyclopropanecarbonyl chloride (0.413 g, 3.95 mmol) were added to (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) 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 fraction was separated, dried, filtered, and concentrated. The crude residue was purified by reverse phase chromatography (Biotage SP4, C-18 25M+, 5-95% CH3CN/water) to give (R)-tert-butyl 1-(5-chloro-3-(cyclopropanecarboxamido)-1H-pyrrolo[2,3-b]pyridin-4-yl)piperidin-3-yl(methyl)carbamate (0.170 g, 48% yield).

Workup

  1. stirringthe reaction was stirred for 10 minutes
  2. customthe organic fraction 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-840befeafa3b4b7580e8f016f7f4a13c
Source dataset
uspto-grants-2014_06
Patent number
US08758830B2

Reaction notes

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