Water → 6-{2-[2-amino-5-(1-methyl-1H-pyrazol-4-yl)pyridin-3-yl]-3H-benzimidazol-5-yl}-5-methyl-4,5-dihydro-2H-pyridazin-3-one

HRID 241403Notes

Reaction equation

HRID 241403 reaction equation
S([O-])(O)=O.[Na+].[NH2:6][C:7]1[C:12]([CH:13]=O)=[CH:11][C:10]([C:15]2[CH:16]=[N:17][N:18]([CH3:20])[CH:19]=2)=[CH:9][N:8]=1.[NH2:21][C:22]1[CH:23]=[C:24]([C:29]2[CH:30]([CH3:36])[CH2:31][C:32](=[O:35])[NH:33][N:34]=2)[CH:25]=[CH:26][C:27]=1[NH2:28].O>CN(C=O)C>[NH2:6][C:7]1[C:12]([C:13]2[NH:21][C:22]3[CH:23]=[C:24]([C:29]4[CH:30]([CH3:36])[CH2:31][C:32](=[O:35])[NH:33][N:34]=4)[CH:25]=[CH:26][C:27]=3[N:28]=2)=[CH:11][C:10]([C:15]2[CH:16]=[N:17][N:18]([CH3:20])[CH:19]=2)=[CH:9][N:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 34410526-(3,4-Diaminophenyl)-5-methyl-4,5-dihydropyridazin-3(2H)-oneHCID 23665763Sodium BisulfiteHCID 866648042-amino-5-(1-methyl-1H-pyrazol-4-yl)pyridine-3-carbaldehyde

Product 1

HCID 668699816-{2-[2-amino-5-(1-methyl-1H-pyrazol-4-yl)pyridin-3-yl]-3H-benzimidazol-5-yl}-5-methyl-4,5-dihydro-2H-pyridazin-3-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.2 300 μl (1.485 mmol) of 38-40% sodium hydrogensulfite solution are added to a solution of 100 mg (0.495 mmol) of 2-amino-5-(1-methyl-1H-pyrazol-4-yl)pyridine-3-carbaldehyde and 108 mg (0.495 mmol) of 6-(3,4-diaminophenyl)-5-methyl-4,5-dihydro-2H-pyridazin-3-one in 4 ml of DMF, and the resultant suspension is stirred at 50° C. for 72 hours. The reaction mixture is cooled to RT, water is added, and the precipitated product is filtered off with suction, washed with water and dried, giving 6-{2-[2-amino-5-(1-methyl-1H-pyrazol-4-yl)pyridin-3-yl]-3H-benzimidazol-5-yl}-5-methyl-4,5-dihydro-2H-pyridazin-3-one as yellow solid; APCI-401;

Workup

  1. filtrationthe precipitated product is filtered off with suction
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-b6957b1528204024af7f274bba9f11af
Source dataset
uspto-grants-2014_02
Patent number
US08648201B2

Reaction notes

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