3-cyclopropyl-1H-pyrazol-5-amine → HCID 58169506, compound

HRID 1484978Notes

Reaction equation

HRID 1484978 reaction equation
Br[C:2]1[C:7]([Cl:8])=[CH:6][N:5]=[C:4]([C:9]2[S:13][C:12]([S:14]([NH:17][NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])(=[O:16])=[O:15])=[CH:11][CH:10]=2)[N:3]=1.[CH:26]1([C:29]2[NH:33][N:32]=[C:31]([NH2:34])[CH:30]=2)[CH2:28][CH2:27]1>C(O)CCC>[Cl:8][C:7]1[C:2]([NH:34][C:31]2[CH:30]=[C:29]([CH:26]3[CH2:28][CH2:27]3)[NH:33][N:32]=2)=[N:3][C:4]([C:9]2[S:13][C:12]([S:14]([NH:17][NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])(=[O:16])=[O:15])=[CH:11][CH:10]=2)=[N:5][CH:6]=1

Participants

4

Reactant 2

HCID 27580143-cyclopropyl-1H-pyrazol-5-amineHCID 58169261HCID 58169261, compound

Product 1

HCID 58169506HCID 58169506, compoundYield 12%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of tert-butyl 2-(5-(4-bromo-5-chloropyrimidin-2-yl)thiophen-2-ylsulfonyl)hydrazinecarboxylate (179 mg, 0.38 mmol, 1.0 eq) and 5-cyclopropyl-1H-pyrazol-3-amine (92 mg, 0.76 mmol, 2.0 equiv.) in n-butanol was refluxed for 2 h, The reaction was cooled down and extracted with EA and the combined layers were dried (Na2SO4), filtered and purified by silica gel chromatography (EA/PE 1:2) to afford tert-butyl 2-(5-(5-chloro-4-(5-cyclopropyl-1H-pyrazol-3-ylamino)pyrimidin-2-yl)thiophen-2-ylsulfonyl)hydrazinecarboxylate (23 mg, 12%). LC-MS (m/z)=512 [M+H]+.

Workup

  1. temperaturewas refluxed for 2 h
  2. temperatureThe reaction was cooled down
  3. extractionextracted with EA
  4. dry with materialthe combined layers were dried (Na2SO4)
  5. filtrationfiltered
  6. custompurified by silica gel chromatography (EA/PE 1:2)

Sources & evidence

ORD record
ord-df6801a51de54e39a5e1a3cfa6d7c348
Source dataset
uspto-grants-2016_08
Patent number
US09422271B2

Reaction notes

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