Pyridine → [3-(N,N-dimethylsulfamoyl)-phenyl]-[3-(4-methoxy-phenyl)-[1,2,4]triazolo[3,4-a]phthalazin-6-yl]-amine

HRID 424401Notes

Reaction equation

HRID 424401 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:13]3[N:14]=[C:15]([NH:22][C:23]4[CH:28]=[CH:27][CH:26]=[C:25](N)[CH:24]=4)[C:16]4[C:21]([C:12]3=[N:11][N:10]=2)=[CH:20][CH:19]=[CH:18][CH:17]=4)=[CH:5][CH:4]=1.N1C=CC=CC=1.C(#N)C.[CH3:39][N:40]([CH3:45])[S:41](Cl)(=[O:43])=[O:42]>CN(C1C=CN=CC=1)C.ClCCl>[CH3:39][N:40]([CH3:45])[S:41]([C:25]1[CH:24]=[C:23]([NH:22][C:15]2[C:16]3[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:12]3=[N:11][N:10]=[C:9]([C:6]4[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=4)[N:13]3[N:14]=2)[CH:28]=[CH:27][CH:26]=1)(=[O:43])=[O:42]

Participants

7

Reactant 4

HCID 1049PyridineHCID 6342AcetonitrileHCID 83372Dimethylsulphamoyl chlorideHCID 66703836N-[3-(4-Methoxyphenyl)-[1,2,4]triazolo[3,4-a]phthalazin-6-yl]benzene-1,3-diamine2×

Product 1

HCID 11576490[3-(N,N-dimethylsulfamoyl)-phenyl]-[3-(4-methoxy-phenyl)-[1,2,4]triazolo[3,4-a]phthalazin-6-yl]-amine

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a suspension of N-[3-(4-methoxyphenyl)-[1,2,4]triazolo[3,4-a]phthalazin-6-yl]-benzene-1,3-diamine (compound A2) (1.90 g) and DMAP (304 mg) in a 3:1:1 mixture of anhydrous pyridine, anhydrous acetonitrile and anhydrous dichloromethane (100 mL) is added dimethylsulfamoyl chloride (2.67 mL). The mixture is stirred at RT for 3 days and filtered. The filtrate is concentrated in vacuum and a non-saturated solution of NaHCO3 (250 mL) is added to the residue. The suspension is filtered and the solid washed with a minimum of MeOH and AcOEt. Purification of residue by column chromatography (CH2Cl2/MeOH, 98:2) gives 1.43 g of the title compound as white powder.

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate is concentrated in vacuum
  3. additiona non-saturated solution of NaHCO3 (250 mL) is added to the residue
  4. filtrationThe suspension is filtered
  5. washthe solid washed with a minimum of MeOH and AcOEt
  6. customPurification of residue by column chromatography (CH2Cl2/MeOH, 98:2)

Sources & evidence

ORD record
ord-364af0cc41d546e08e557a8f6c772fbe
Source dataset
uspto-grants-2012_01
Patent number
US08106047B2

Reaction notes

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