1-Butanesulfonyl chloride → HCID 178455637, compound

HRID 255009Notes

Reaction equation

HRID 255009 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-560a85f6388e4847a3e1c9f5d9548b60
Source dataset
uspto-grants-2011_01
Patent number
US07875728B2

Reaction notes

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