1H-Indazol-5-amine → Rho-Kinase-IN-3

HRID 734659노트

반응식

HRID 734659 반응식
[CH3:1][C:2]1[NH:3][C:4](=[O:21])[CH2:5][CH:6]([C:11]2[CH:20]=[CH:19][C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=2)[C:7]=1[C:8](O)=[O:9].[NH:22]1[C:30]2[C:25](=[CH:26][C:27]([NH2:31])=[CH:28][CH:29]=2)[CH:24]=[N:23]1>CN(C=O)C>[NH:22]1[C:30]2[C:25](=[CH:26][C:27]([NH:31][C:8]([C:7]3[CH:6]([C:11]4[CH:20]=[CH:19][C:18]5[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=5)[CH:12]=4)[CH2:5][C:4](=[O:21])[NH:3][C:2]=3[CH3:1])=[O:9])=[CH:28][CH:29]=2)[CH:24]=[N:23]1

참가 물질

4

반응물 2

HCID 880121H-Indazol-5-amineHCID 160998652-Methyl-4-(2-naphthalenyl)-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxylic acid

생성물 1

HCID 11269477Rho-Kinase-IN-3수율 22.1%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

The product of step 2 (450 mg, 1.60 mmol, 1 equiv) was combined with 1H-indazol-5-amine (212 mg, 1.60 mmol, 1 equiv) and polystyrene-bound carbodiimide (1.78 g, 1.1 mmol/g, 1.97 mmol, 1.2 equiv) in 6 mL DMF. The reaction mixture was stirred for 22 hours at room temperature. The resin was removed by filtration and washed alternately with CH2Cl2 and MeOH, ending with CH2Cl2. The volatile solvents were removed en vacuo and water was added, providing a solid residue. The residue was triturated with ethyl acetate, affording 140 mg of the title compound as a white crystalline solid. MS (ES+) m/e 397 [M+H]+

후처리

  1. customThe resin was removed by filtration
  2. washwashed alternately with CH2Cl2 and MeOH
  3. customThe volatile solvents were removed en vacuo and water
  4. additionwas added
  5. customproviding a solid residue
  6. customThe residue was triturated with ethyl acetate

출처 및 근거

ORD 기록
ord-5716b9cbeb704cdc87f8e54ddf2adac0
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07592357B2

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