1,4-Dioxane hydrochloride → 2-Hydroxy-N-[5-(7-isopropyl-7H-pyrrolo[2,3-d]pyrimidine-5-carbonyl)-pyridin-3-yl]-2-phenyl-acetamide

HRID 82126Notes

Reaction equation

HRID 82126 reaction equation
[CH:1]([N:4]1[C:8]2[N:9]=[CH:10][N:11]=[CH:12][C:7]=2[C:6]([C:13]([C:15]2[CH:16]=[C:17]([NH:21][C:22](=[O:37])[CH:23]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[O:24]C3CCCCO3)[CH:18]=[N:19][CH:20]=2)=[O:14])=[CH:5]1)([CH3:3])[CH3:2].Cl.O1CCOCC1>O1CCOCC1>[OH:24][CH:23]([C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)[C:22]([NH:21][C:17]1[CH:18]=[N:19][CH:20]=[C:15]([C:13]([C:6]2[C:7]3[CH:12]=[N:11][CH:10]=[N:9][C:8]=3[N:4]([CH:1]([CH3:3])[CH3:2])[CH:5]=2)=[O:14])[CH:16]=1)=[O:37]

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 70817713HCID 70817713, compound

Product 1

HCID 708177122-Hydroxy-N-[5-(7-isopropyl-7H-pyrrolo[2,3-d]pyrimidine-5-carbonyl)-pyridin-3-yl]-2-phenyl-acetamideYield 78%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To stirred solution of N-[5-(7-Isopropyl-7H-pyrrolo[2,3-d]pyrimidine-5-carbonyl)-pyridin-3-yl]-2-phenyl-2-(tetrahydro-pyran-2-yloxy)-acetamide (60 mg, 0.12 mmol) (Preparation 237) in dioxane (1 mL) was added dioxane-HCl (1 mL of a 4N solution) at 00° C. The mixture was stirred at room temperature for 2 hours. All the volatiles were removed in vacuo and the solid obtained was triturated with diethyl ether to afford the title compound as a yellowish solid in 78% yield, 42 mg.

Workup

  1. customAll the volatiles were removed in vacuo
  2. customthe solid obtained
  3. customwas triturated with diethyl ether

Sources & evidence

ORD record
ord-453a882a1700449f8f6dcee87a2d2b65
Source dataset
uspto-grants-2014_09
Patent number
US08846698B2

Reaction notes

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