Hydrochloric Acid → HCID 178466733, compound

HRID 511034Notes

Reaction equation

HRID 511034 reaction equation
[Cl:1][C:2]1[C:3]([F:37])=[C:4]([C:29]2[CH:30]=[CH:31][C:32]([C:35]#N)=[N:33][CH:34]=2)[C:5]([O:26][CH2:27][CH3:28])=[C:6]([CH:8]([NH:10][C:11]2[N:19]=[CH:18][N:17]=[C:16]3[C:12]=2[N:13]=[CH:14][N:15]3C2CCCCO2)[CH3:9])[CH:7]=1.[OH-:38].[Na+].[OH2:40].Cl>C(O)C>[Cl:1][C:2]1[C:3]([F:37])=[C:4]([C:29]2[CH:30]=[CH:31][C:32]([C:35]([OH:40])=[O:38])=[N:33][CH:34]=2)[C:5]([O:26][CH2:27][CH3:28])=[C:6]([CH:8]([NH:10][C:11]2[N:19]=[CH:18][N:17]=[C:16]3[C:12]=2[N:13]=[CH:14][NH:15]3)[CH3:9])[CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 962Water3×HCID 14798Sodium HydroxideHCID 86666953HCID 86666953, compound

Product 1

HCID 178466733HCID 178466733, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

A solution of 5-[3-chloro-6-ethoxy-2-fluoro-5-(1-{[9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-yl]amino}ethyl)phenyl]pyridine-2-carbonitrile (0.070 g, 0.13 mmol) in ethanol (1.2 mL) was treated with 3 M sodium hydroxide in water (0.6 mL, 2 mmol) and stirred at 90° C. for 4 h in a sealed tube. The reaction mixture was cooled to 0° C., quenched with 12 M HCl in water (0.1 mL, 2 mmol), and stirred at 20° C. for 30 minutes. The reaction mixture was treated with additional 12 M HCl in water (0.2 mL, 2 mmol) and stirred at 20° C. for 15 minutes. The reaction mixture was concentrated to give the desired product (61 mg, quantitative) which was used without further purification. LCMS for C21H19ClFN6O3 (M+H)+: m/z=457.1. Found: 457.1.

Workup

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. stirringstirred at 20° C. for 30 minutes
  3. stirringstirred at 20° C. for 15 minutes
  4. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-f2444665dcb74d9db2941c185d487da4
Source dataset
uspto-grants-2015_08
Patent number
US09096600B2

Reaction notes

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