Pyridine → HCID 67082125, compound

HRID 2203950Notes

Reaction equation

HRID 2203950 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-994f717c1b044c3eb165ebe9be12abd0
Source dataset
uspto-grants-2016_06
Patent number
US09365568B2

Reaction notes

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