Hydrochloric Acid → HCID 67502358, compound

HRID 1631386Notes

Reaction equation

HRID 1631386 reaction equation
[C:1]([NH:5][C:6]([C:8]1[CH:9]=[N:10][N:11]2[CH:16]=[CH:15][C:14]([N:17]3[CH2:21][CH2:20][CH2:19][C@@H:18]3[C:22]3[C:23]([O:29]C)=[N:24][CH:25]=[C:26]([F:28])[CH:27]=3)=[N:13][C:12]=12)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl>O1CCOCC1>[C:1]([NH:5][C:6]([C:8]1[CH:9]=[N:10][N:11]2[CH:16]=[CH:15][C:14]([N:17]3[CH2:21][CH2:20][CH2:19][C@@H:18]3[C:22]3[C:23](=[O:29])[NH:24][CH:25]=[C:26]([F:28])[CH:27]=3)=[N:13][C:12]=12)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 66847822HCID 66847822, compound

Product 1

HCID 67502358HCID 67502358, compoundYield 85.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

A pressure flask was charged with (R)—N-tert-butyl-5-(2-(5-fluoro-2-methoxypyridin-3-yl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide (Example 80, 10 mg, 0.024 mmol), dioxane (0.7 mL) and 2M HCl (0.100 mL, 0.200 mmol). The flask was sealed and the reaction mixture was stirred at 80° C. for 5 days. The mixture was cooled to ambient temperature and concentrated. The residue was purified by reverse-phase column chromatography (0-50% acetonitrile/water) to afford the title compound (8.2 mg, 85%). MS (apci) m/z=399.1 (M+H).

Workup

  1. customThe flask was sealed
  2. temperatureThe mixture was cooled to ambient temperature
  3. concentrationconcentrated
  4. customThe residue was purified by reverse-phase column chromatography (0-50% acetonitrile/water)

Sources & evidence

ORD record
ord-226439813ba04a609813241478c95d43
Source dataset
uspto-grants-2014_07
Patent number
US08791123B2

Reaction notes

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