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1,2-Dichloroethane → HCID 178429199, 화합물

HRID 734717
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HRID 734717 반응식
[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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 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

생성물 1

HCID 178429199HCID 178429199, 화합물수율 5%

시약·촉매·용매 3

HCID 313
Hydrochloric Acid
용매
HCID 6228Dimethylformamide용매
HCID 8857Ethyl Acetate용매

실험 절차

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]+

후처리

  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)

출처 및 근거

ORD 기록
ord-231831db362b44c69582cfcd38de86ea
출처 데이터셋
uspto-grants-2009_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07592357B2

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