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

HRID 241407Notes

Reaction equation

HRID 241407 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]([CH2:20][C:21](=[O:28])[N:22]3[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]3)[CH:19]=2)=[CH:9][N:8]=1.[NH2:29][C:30]1[CH:31]=[C:32]([C:37]2[CH:38]([CH3:44])[CH2:39][C:40](=[O:43])[NH:41][N:42]=2)[CH:33]=[CH:34][C:35]=1[NH2:36].O>CN(C=O)C>[NH2:6][C:7]1[C:12]([C:13]2[NH:29][C:30]3[CH:31]=[C:32]([C:37]4[CH:38]([CH3:44])[CH2:39][C:40](=[O:43])[NH:41][N:42]=4)[CH:33]=[CH:34][C:35]=3[N:36]=2)=[CH:11][C:10]([C:15]2[CH:16]=[N:17][N:18]([CH2:20][C:21](=[O:28])[N:22]3[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]3)[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 866648052-amino-5-[1-(2-oxo-2-piperidin-1-ylethyl)-1H-pyrazol-4-yl]pyridine-3-carbaldehyde

Product 1

HCID 509233096-(2-{2-amino-5-[1-(2-oxo-2-piperidin-1-ylethyl)-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

5.2 110.07 μl (0.558 mmol) of 38-40% sodium hydrogensulfite solution are added to a solution of 70 mg (0.223 mmol) of 2-amino-5-[1-(2-oxo-2-piperidin-1-ylethyl)-1H-pyrazol-4-yl]pyridine-3-carbaldehyde and 58.51 mg (0.268 mmol) of 6-(3,4-diaminophenyl)-5-methyl-4,5-dihydro-2H-pyridazin-3-one in 3 ml DMF, and the mixture is irradiated with microwaves for 30 min at 120° C. in the Biotage SmithSynthesizer. The reaction mixture is cooled to room temperature, and water is added. The precipitate is filtered off and washed with water and subsequently dried. The residue is purified by means of RP-HPLC: 6-(2-{2-amino-5-[1-(2-oxo-2-piperidin-1-ylethyl)-1H-pyrazol-4-yl]pyridin-3-yl}-3H-benzimidazol-5-yl)-5-methyl-4,5-dihydro-2H-pyridazin-3-one as yellow solid; HPLC-MS [M+H]+ 512.2;

Workup

  1. customthe mixture is irradiated with microwaves for 30 min at 120° C. in the Biotage SmithSynthesizer
  2. filtrationThe precipitate is filtered off
  3. washwashed with water
  4. customsubsequently dried
  5. customThe residue is purified by means of RP-HPLC

Sources & evidence

ORD record
ord-b3020dfefdde46588362d792fa173a2b
Source dataset
uspto-grants-2014_02
Patent number
US08648201B2

Reaction notes

Loading…