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1,2-Dichloroethane → N-(3-Chloro-6-fluoro-1H-indazol-5-yl)-4-(4-chloro-2-fluorophenyl)-2-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide

HRID 734705
ノート
印刷プレビュー

反応式

HRID 734705 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][C:12](=[O:14])[NH:11][C:10]([CH3:15])=[C:9]2[C:16]([OH:18])=O)=[C:4]([F:19])[CH:3]=1.[Cl:20][C:21]1[C:29]2[C:24](=[CH:25][C:26]([F:31])=[C:27]([NH2:30])[CH:28]=2)[NH:23][N:22]=1.C(Cl)CCl.CCN(CC)CC>CN(C=O)C.CCOC(C)=O.Cl>[Cl:20][C:21]1[C:29]2[C:24](=[CH:25][C:26]([F:31])=[C:27]([NH:30][C:16]([C:9]3[CH:8]([C:5]4[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][C:4]=4[F:19])[CH2:13][C:12](=[O:14])[NH:11][C:10]=3[CH3:15])=[O:18])[CH:28]=2)[NH:23][N:22]=1
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 688260574-(4-Chloro-2-fluorophenyl)-2-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxylic acidHCID 1785072033-chloro-6-fluoro-1H-indazol-5-amine

生成物 1

HCID 178429202N-(3-Chloro-6-fluoro-1H-indazol-5-yl)-4-(4-chloro-2-fluorophenyl)-2-methyl-6-oxo-1,4,5,6-tetrahydro-3-pyridinecarboxamide収率 7%

試薬・触媒・溶媒 3

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

実験手順

The product of Example 3 Step 2 (191 mg, 0.668 mmol, 1.00 equiv), the product of Step 2 (125 mg, 0.668 mmol, 1.0 equiv), and EDC (153 mg, 0.802 mmol, 1.20 equiv) were suspended in 2.0 mL DMF. Et3N (0.112 mL, 0.802 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 reverse-phase HPLC (20-90% CH3CN/H2O—NH4OH to pH 10 over 13 minutes, retention time 7.79 min) to provide 20 mg (7%) of the title compound as a white solid. MS (ES+) m/e 452 [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 reverse-phase HPLC (20-90% CH3CN/H2O—NH4OH to pH 10 over 13 minutes, retention time 7.79 min)

出典と根拠

ORDレコード
ord-8d585ffb8f87406eb6d71dbecbadcc4d
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

読み込み中…

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