Dichloromethane → HCID 67340833, compound

HRID 1674974Notes

Reaction equation

HRID 1674974 reaction equation
[CH3:1][N:2]([CH3:7])[S:3](Cl)(=[O:5])=[O:4].ClCCl.[CH2:11]1[CH:15]2[CH2:16][NH:17][CH2:18][CH:14]2[CH2:13][N:12]1[C:19]1[CH:20]=[CH:21][C:22]2[N:23]([C:25]([C:28]([F:31])([F:30])[F:29])=[N:26][N:27]=2)[N:24]=1>C1(C)C=CC=CC=1>[CH3:1][N:2]([CH3:7])[S:3]([N:17]1[CH2:16][CH:15]2[CH2:11][N:12]([C:19]3[CH:20]=[CH:21][C:22]4=[N:27][N:26]=[C:25]([C:28]([F:31])([F:29])[F:30])[N:23]4[N:24]=3)[CH2:13][CH:14]2[CH2:18]1)(=[O:5])=[O:4]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 83372Dimethylsulphamoyl chlorideHCID 673403076-(hexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl)-3-(trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazine

Product 1

HCID 67340833HCID 67340833, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

N,N-Dimethylsulfamoyl chloride (0.027 g, 0.19 mmol) and then dichloromethane were added sequentially to a mixture of diisopropylethylamineamine (0.044 g, 0.34 mmol) and 6-(hexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl)-3-(trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazine (0.05 g, 0.17 mmol) in toluene (1.5 mL). The reaction mixture was stirred for 1 hour and evaporated to give an involatile residue. The residue was purified by preparative hplc using a Phenomenex Luna C18 100A column (10μ silica, 21 mm diameter, 150 mm length) eluted with decreasingly polar mixtures of water (containing 0.1% trifluoroacetic acid) and acetonitrile as eluents to give N,N-dimethyl-2-[3-(trifluoromethyl)-[1,2,4]triazolo[3,4-f]pyridazin-6-yl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-sulfonamide (0.0206 g, 30%) as a white solid.

Workup

  1. customevaporated
  2. customto give an involatile residue
  3. customThe residue was purified by preparative hplc
  4. washeluted with decreasingly polar mixtures of water (containing 0.1% trifluoroacetic acid) and acetonitrile as eluents

Sources & evidence

ORD record
ord-bac84b3b875b401ea7a2a0d2694c73a9
Source dataset
uspto-grants-2011_08
Patent number
US08003649B2

Reaction notes

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