Water → 7-Chloro-5-((3-methyl-1H-indol-7-yl)amino)pyrido[3,4-d]pyridazin-4(3H)-one

HRID 629202Notes

Reaction equation

HRID 629202 reaction equation
Cl[C:2]1[C:7]2[C:8](=[O:12])[NH:9][N:10]=[CH:11][C:6]=2[CH:5]=[C:4]([Cl:13])[N:3]=1.CCN(C(C)C)C(C)C.[CH3:23][C:24]1[C:32]2[C:27](=[C:28]([NH2:33])[CH:29]=[CH:30][CH:31]=2)[NH:26][CH:25]=1.O>CS(C)=O>[Cl:13][C:4]1[N:3]=[C:2]([NH:33][C:28]2[CH:29]=[CH:30][CH:31]=[C:32]3[C:27]=2[NH:26][CH:25]=[C:24]3[CH3:23])[C:7]2[C:8](=[O:12])[NH:9][N:10]=[CH:11][C:6]=2[CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 186125633-methyl-1H-indol-7-amineHCID 887689205,7-Dichloropyrido[3,4-d]pyridazin-4(3H)-one

Product 1

HCID 899724117-Chloro-5-((3-methyl-1H-indol-7-yl)amino)pyrido[3,4-d]pyridazin-4(3H)-one

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
140 °C

Procedure

To 5,7-dichloro-3H-pyrido[3,4-d]pyridazin-4-one (180 mg, 0.833 mmol) in DMSO (1 ml) in a sealable vial, was added DIPEA (0.189 ml, 1.083 mmol) and 3-methyl-1H-indol-7-amine (158 mg, 1.083 mmol). The vial was capped to close and the mixture heated on a sandbath at 140° C. for 1 h. The resultant mixture was poured into water (20 ml), and extracted with EtOAc (20 ml). Organic phase was washed with water then brine, dried over Na2SO4, then concentrated under vacuum. The residue was triterated with DCM, then collected by filtration and dried to give title compound as a yellow-mustard coloured solid.

Workup

  1. customThe vial was capped
  2. customto close
  3. extractionextracted with EtOAc (20 ml)
  4. washOrganic phase was washed with water
  5. dry with materialbrine, dried over Na2SO4
  6. concentrationconcentrated under vacuum
  7. filtrationcollected by filtration
  8. customdried

Sources & evidence

ORD record
ord-0832cdb1abcb49aa8bc2962099f71763
Source dataset
uspto-grants-2016_04
Patent number
US09315500B2

Reaction notes

Loading…