Dichloromethane → HCID 67340839, compound

HRID 1674975Notes

Reaction equation

HRID 1674975 reaction equation
[CH2:1]([S:3](Cl)(=[O:5])=[O:4])[CH3:2].ClCCl.C(N(C(C)C)CC)(C)C.[CH2:19]1[CH:23]2[CH2:24][NH:25][CH2:26][CH:22]2[CH2:21][N:20]1[C:27]1[CH:28]=[CH:29][C:30]2[N:31]([C:33]([C:36]([F:39])([F:38])[F:37])=[N:34][N:35]=2)[N:32]=1>C1(C)C=CC=CC=1>[CH2:1]([S:3]([N:25]1[CH2:24][CH:23]2[CH2:19][N:20]([C:27]3[CH:28]=[CH:29][C:30]4=[N:35][N:34]=[C:33]([C:36]([F:39])([F:37])[F:38])[N:31]4[N:32]=3)[CH2:21][CH:22]2[CH2:26]1)(=[O:5])=[O:4])[CH3:2]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 11667Ethanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 673403076-(hexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl)-3-(trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazine

Product 1

HCID 67340839HCID 67340839, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Ethanesulfonyl chloride (0.024 g, 0.19 mmol) and then dichloromethane (0.5 mL) were added sequentially to a mixture of diisopropylethylamine (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 (0.050 g, 0.17 mmol) in toluene (1.5 mL). The reaction mixture was stirred for 1 hour at ambient temperature and then for 1.5 hours at 50° C. and then 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 6-(5-ethylsulfonyl-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrol-2-yl)-3-(trifluoromethyl)-[1,2,4]triazolo[3,4-f]pyridazine (0.0143 g, 22%) as a white solid.

Workup

  1. waitfor 1.5 hours at 50° C.
  2. customevaporated
  3. customto give an involatile residue
  4. customThe residue was purified by preparative hplc
  5. washeluted with decreasingly polar mixtures of water (containing 0.1% trifluoroacetic acid) and acetonitrile as eluents

Sources & evidence

ORD record
ord-c085b281666e4abf9b0edbc2534b34a0
Source dataset
uspto-grants-2011_08
Patent number
US08003649B2

Reaction notes

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