3-cyclopropyl-1H-pyrazol-5-amine → HCID 58169492, compound

HRID 1484894Notes

Reaction equation

HRID 1484894 reaction equation
[C:1]([NH:5][S:6]([C:9]1[O:10][C:11]([C:14]2[N:19]=[C:18](S(C)=O)[C:17]([Cl:23])=[CH:16][N:15]=2)=[CH:12][CH:13]=1)(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:24]1([C:27]2[NH:31][N:30]=[C:29]([NH2:32])[CH:28]=2)[CH2:26][CH2:25]1>C(O)CCC>[C:1]([NH:5][S:6]([C:9]1[O:10][C:11]([C:14]2[N:19]=[C:18]([NH:32][C:29]3[CH:28]=[C:27]([CH:24]4[CH2:26][CH2:25]4)[NH:31][N:30]=3)[C:17]([Cl:23])=[CH:16][N:15]=2)=[CH:12][CH:13]=1)(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 27580143-cyclopropyl-1H-pyrazol-5-amineHCID 58169321HCID 58169321, compound

Product 1

HCID 58169492HCID 58169492, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
90 °C

Procedure

The mixture of the crude N-tert-butyl-5-(5-chloro-4-(methylsulfinyl)pyrimidin-2-yl)furan-2-sulfonamide and 5-cyclopropyl-1H-pyrazol-3-amine (255 mg, 2.08 mmol, 5.0 equiv.) in n-butanol (6 mL) was stirred at 90° C. for 2 h, then, partitioned between brine and ethylacetate. The organic layer was washed over brine, dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography to afford N-tert-butyl-5-(5-chloro-4-(5-cyclopropyl-1H-pyrazol-3-ylamino)pyrimidin-2-yl)furan-2-sulfonamide (45 mg, 28% over 2 steps). LC-MS (m/z)=437.0 [M+H]+.

Workup

  1. custompartitioned between brine and ethylacetate
  2. washThe organic layer was washed over brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-c68f70c241c44feab539f14ba71e5b52
Source dataset
uspto-grants-2016_08
Patent number
US09422271B2

Reaction notes

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