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1,2-Dichloroethane → Dihydropyridone indazole amide 13

HRID 734678
ノート
印刷プレビュー

反応式

HRID 734678 の反応式
[F:1][C:2]([F:21])([F:20])[C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:14][C:13](=[O:15])[NH:12][C:11]([CH3:16])=[C:10]2[C:17](O)=[O:18])=[CH:5][CH:4]=1.[NH2:22][C:23]1[CH:24]=[C:25]2[C:29](=[CH:30][CH:31]=1)[NH:28][N:27]=[C:26]2[CH3:32].C(Cl)CCl.CCN(CC)CC>CN(C=O)C.CCOC(C)=O.Cl>[CH3:16][C:11]1[NH:12][C:13](=[O:15])[CH2:14][CH:9]([C:6]2[CH:5]=[CH:4][C:3]([C:2]([F:20])([F:21])[F:1])=[CH:8][CH:7]=2)[C:10]=1[C:17]([NH:22][C:23]1[CH:24]=[C:25]2[C:29](=[CH:30][CH:31]=1)[NH:28][N:27]=[C:26]2[CH3:32])=[O:18]
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 160998632-Methyl-6-oxo-4-(4-(trifluoromethyl)phenyl)-1,4,5,6-tetrahydropyridine-3-carboxylic acidHCID 178434299HCID 178434299、化合物

生成物 1

HCID 178429233Dihydropyridone indazole amide 13収率 6%

試薬・触媒・溶媒 3

HCID 313
Hydrochloric Acid
溶媒
HCID 6228Dimethylformamide溶媒
HCID 8857Ethyl Acetate溶媒

実験手順

The product of Example 5, Step 2 (225 mg, 0.75 mmol, 1.00 equiv), 5-amino-3-methylindazole (110 mg, 0.75 mmol, 1.0 equiv), and EDC (172 mg, 0.90 mmol, 1.20 equiv) were suspended in 2.0 mL DMF. Et3N (0.125 mL, 0.90 mmol, 1.2 equiv) was added and the solution was stirred at room temperature for 18 hrs. The reaction mixture was diluted with EtOAc and 1N HCl. The phases were separated, and the organic phase was washed twice with 1N HCl, once with satd. NaHCO3, and once with satd. NaCl. The organic phase was dried over Na2SO4, filtered, and concentrated en vacuo. The residue was purified by flash chromatography (20-100% EtOAc in Hexanes) and further purified by reverse-phase HPLC (10-70% CH3CN/H2O—NH4OH to pH 10 over 20 minutes, retention time 11.74 min) to provide 18 mg (6%) of the title compound as a white solid. MS (ES+) m/e 429 [M+H]+

後処理

  1. customThe phases were separated
  2. washthe organic phase was washed twice with 1N HCl, once with satd
  3. dry with materialThe organic phase was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated en vacuo
  6. customThe residue was purified by flash chromatography (20-100% EtOAc in Hexanes)
  7. customfurther purified by reverse-phase HPLC (10-70% CH3CN/H2O—NH4OH to pH 10 over 20 minutes, retention time 11.74 min)

出典と根拠

ORDレコード
ord-886a75f79ad04808aff51f605bfd94f4
出典データセット
uspto-grants-2009_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07592357B2

反応ノート

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