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1,2-Dichloroethane → HCID 178429199、化合物

HRID 734717
ノート
印刷プレビュー

反応式

HRID 734717 の反応式
[Cl:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([F:12])=[C:8]([NH2:11])[CH:9]=2)[NH:4][N:3]=1.[F:13][C:14]([F:33])([F:32])[C:15]1[CH:20]=[CH:19][C:18]([CH:21]2[CH2:26][C:25](=[O:27])[NH:24][C:23]([CH3:28])=[C:22]2[C:29](O)=[O:30])=[CH:17][CH:16]=1.C(Cl)CCl.CCN(CC)CC>CN(C=O)C.CCOC(C)=O.Cl>[Cl:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([F:12])=[C:8]([NH:11][C:29]([C:22]3[CH:21]([C:18]4[CH:19]=[CH:20][C:15]([C:14]([F:33])([F:13])[F:32])=[CH:16][CH:17]=4)[CH2:26][C:25](=[O:27])[NH:24][C:23]=3[CH3:28])=[O:30])[CH:9]=2)[NH:4][N:3]=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 160998632-Methyl-6-oxo-4-(4-(trifluoromethyl)phenyl)-1,4,5,6-tetrahydropyridine-3-carboxylic acidHCID 1785072033-chloro-6-fluoro-1H-indazol-5-amine

生成物 1

HCID 178429199HCID 178429199、化合物収率 5%

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 from Example 39, Step 2 (125 mg, 0.668 mmol, 1.0 equiv) was combined with the product from Example 5, Step 2 (200 mg, 0.668 mmol, 1.0 equiv), EDC (153 mg, 0.802 mmol, 1.2 equiv) and Et3N (112 μL, 0.802 mmol, 1.2 equiv) in DMF (2 mL) and stirred at room temperature for 18 hours. 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 concentrated en vacuo. The residue was purified by flash chromatography (20-100% EtOAc in Hexanes) and further purified by reverse-phase HPLC (10-75% CH3CN/H2O, 0.1% TFA over 20 minutes, retention time 13.9 min) to provide 15 mg (5%) of the title compound as a white solid. MS (ES+) m/e 467 [M+H]+

後処理

  1. customThe phases were separated
  2. washthe organic phase was washed twice with 1N HCl, once with satd
  3. concentrationThe organic phase was concentrated en vacuo
  4. customThe residue was purified by flash chromatography (20-100% EtOAc in Hexanes)
  5. customfurther purified by reverse-phase HPLC (10-75% CH3CN/H2O, 0.1% TFA over 20 minutes, retention time 13.9 min)

出典と根拠

ORDレコード
ord-231831db362b44c69582cfcd38de86ea
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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