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 241407노트

반응식

HRID 241407 반응식
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

참가 물질

6

반응물 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

생성물 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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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;

후처리

  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

출처 및 근거

ORD 기록
ord-b3020dfefdde46588362d792fa173a2b
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08648201B2

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