HCID 66854087, compound → HCID 66853176, compound

HRID 1631390Notes

Reaction equation

HRID 1631390 reaction equation
[CH:1]1([NH:4][C:5]([C:7]2[CH:8]=[N:9][N:10]3[CH:15]=[CH:14][C:13]([N:16]4[CH2:20][CH2:19][CH2:18][C@@H:17]4[C:21]4[CH:26]=[C:25]([F:27])[CH:24]=[C:23]([O:28][CH2:29][CH:30]5[CH2:34][O:33]C(C)(C)[O:31]5)[CH:22]=4)=[N:12][C:11]=23)=[O:6])[CH2:3][CH2:2]1>O1CCOCC1.Cl.CCN(C(C)C)C(C)C>[CH:1]1([NH:4][C:5]([C:7]2[CH:8]=[N:9][N:10]3[CH:15]=[CH:14][C:13]([N:16]4[CH2:20][CH2:19][CH2:18][C@@H:17]4[C:21]4[CH:26]=[C:25]([F:27])[CH:24]=[C:23]([O:28][CH2:29][CH:30]([OH:31])[CH2:34][OH:33])[CH:22]=4)=[N:12][C:11]=23)=[O:6])[CH2:3][CH2:2]1

Participants

5

Reactant 1

HCID 66854087HCID 66854087, compound

Product 1

HCID 66853176HCID 66853176, compoundYield 83%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidCatalystHCID 81531DiisopropylethylamineCatalystHCID 312751,4-DioxaneSolvent

Procedure

A solution of N-cyclopropyl-5-((2R)-2-(3-((2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)-5-fluorophenyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide (Example 206, 30 mg, 0.061 mmol) in dioxane (0.5 mL) was charged with two drops of 6N HCl and shaken for two minutes. DIEA (5 drops) was added and the mixture directly purified by reverse phase column chromatography (0-50% acetonitrile/water) to afford N-cyclopropyl-5-((2R)-2-(3-(2,3-dihydroxypropoxy)-5-fluorophenyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide (23 mg, 83% yield) as a clear film. MS (apci) m/z=456.1 (M+H).

Workup

  1. customthe mixture directly purified by reverse phase column chromatography (0-50% acetonitrile/water)

Sources & evidence

ORD record
ord-19a7b1292e704126af2657088135e1c2
Source dataset
uspto-grants-2014_07
Patent number
US08791123B2

Reaction notes

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