3,4,5-Trichloropyridazine → HCID 86702057, compound

HRID 873577Notes

Reaction equation

HRID 873577 reaction equation
[Cl:1][C:2]1[N:3]=[N:4][CH:5]=[C:6](Cl)[C:7]=1[Cl:8].C(N(C(C)C)C(C)C)C.[NH:19]1[CH2:22][CH:21]([C:23]([NH:25][C:26]2[CH:31]=[CH:30][C:29]([S:32]([CH:35]3[CH2:40][CH2:39][N:38]([C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])[CH2:37][CH2:36]3)(=[O:34])=[O:33])=[CH:28][CH:27]=2)=[O:24])[CH2:20]1>CN(C)C=O.O>[Cl:8][C:7]1[C:6]([N:19]2[CH2:22][CH:21]([C:23]([NH:25][C:26]3[CH:27]=[CH:28][C:29]([S:32]([CH:35]4[CH2:36][CH2:37][N:38]([C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])[CH2:39][CH2:40]4)(=[O:34])=[O:33])=[CH:30][CH:31]=3)=[O:24])[CH2:20]2)=[CH:5][N:4]=[N:3][C:2]=1[Cl:1]

Participants

6

Reactant 3

HCID 701113,4,5-TrichloropyridazineHCID 81531DiisopropylethylamineHCID 86702049HCID 86702049, compound

Product 1

HCID 86702057HCID 86702057, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

To 3,4,5-trichloropyridazine (1.624 g, 8.85 mmol) and N-ethyl-N-isopropylpropan-2-amine (2.289 g, 17.71 mmol) in 50 mL N,N-dimethylformamide at 0° C. was added tert-butyl 4-(4-(azetidine-3-carboxamido)phenylsulfonyl)piperidine-1-carboxylate (2.5 g, 5.90 mmol) in 10 ml N,N-dimethylformamide, dropwise. The reaction mixture was stirred from 0° C. to room temperature overnight, diluted with water and extracted with ethyl acetate. The organic layer was dried with magnesium sulfate, filtered, concentrated and purified by flash chromatography to give the title compound.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried with magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified by flash chromatography

Sources & evidence

ORD record
ord-3091970f17a74809994f1c6556936ea7
Source dataset
uspto-grants-2015_03
Patent number
US08975398B2

Reaction notes

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