1-Butanesulfonyl chloride → HCID 178455637, compound

HRID 2095175Notes

Reaction equation

HRID 2095175 reaction equation
[NH2:1][CH2:2][C:3]1[C:4](=[N:9][NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[CH:12]=2)[C:5]([NH2:8])=[N:6][N:7]=1.CCN(C(C)C)C(C)C.[CH2:27]([S:31](Cl)(=[O:33])=[O:32])[CH2:28][CH2:29][CH3:30]>CN(C=O)C>[NH2:8][C:5]1[C:4](=[N:9][NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[CH:12]=2)[C:3]([CH2:2][NH:1][S:31]([CH2:27][CH2:28][CH2:29][CH3:30])(=[O:33])=[O:32])=[N:7][N:6]=1

Participants

5

Reactant 3

HCID 754301-Butanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 178510679HCID 178510679, compound

Product 1

HCID 178455637HCID 178455637, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 5-aminomethyl-4-[(3-fluorophenyl)hydrazono]-4H-pyrazol-3-ylamine (40 mg, 0.17 mmol) in anhydrous DMF (3 mL) was added to a 10 mL reaction vessel containing PS-DIEA (2.5 eq, 150 mg) and butane-1-sulfonyl chloride (1.1 eq, 0.19 mmol) suspended in anhydrous DMF (3 mL). The reaction mixture was stirred at ambient temperature under argon for approximately 16 hours before it was filtered, washed with DMF (3×5 mL) and concentrated under reduced pressure. The resulting yellow residue was recrystallized from ether to yield 13 mg (22%) of the title compound as a yellow powder. MS (m/z, ES+): 355 (M+1, 100%).

Workup

  1. filtrationwas filtered
  2. washwashed with DMF (3×5 mL)
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting yellow residue was recrystallized from ether

Sources & evidence

ORD record
ord-f19838cd7fb642a6b97d1ba3e4fd1e7c
Source dataset
uspto-grants-2013_05
Patent number
US08445694B2

Reaction notes

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