Hydrochloric Acid → HCID 57917295, 화합물

HRID 69266노트

반응식

HRID 69266 반응식
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[N:9]2)=[CH:4][C:3]=1[CH:12]([C:14]1[N:18]2[N:19]=[C:20]([C:23]3[CH:24]=[N:25][N:26]([CH2:28][CH2:29][O:30]C4CCCCO4)[CH:27]=3)[CH:21]=[CH:22][C:17]2=[N:16][CH:15]=1)[CH3:13].Cl>C(Cl)Cl.O1CCOCC1>[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[N:9]2)=[CH:4][C:3]=1[CH:12]([C:14]1[N:18]2[N:19]=[C:20]([C:23]3[CH:24]=[N:25][N:26]([CH2:28][CH2:29][OH:30])[CH:27]=3)[CH:21]=[CH:22][C:17]2=[N:16][CH:15]=1)[CH3:13]

참가 물질

5

반응물 2

HCID 313Hydrochloric AcidHCID 68639506(Rac)-7-fluoro-6-[1-(6-{1-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-1h-pyrazol-4-yl}-imidazo[1,2-b]pyridazin-3-yl)-ethyl]-quinoline

생성물 1

HCID 57917295HCID 57917295, 화합물

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 312751,4-Dioxane용매

실험 절차

To a solution of (rac)-7-fluoro-6-[1-(6-{1-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-1H-pyrazol-4-yl}-imidazo[1,2-b]pyridazin-3-yl)-ethyl]-quinoline (Stage 255.1, 49 mg, 0.101 mmol) in DCM (3 mL) stirred at rt was added a solution of HCl in dioxane (4 M, 0.252 mL). The RM was stirred 1 h at rt, during this time the product precipitated as an oil. The residue was taken in DCM and water, then neutralized with a solution of 10% NaHCO3 and extracted with DCM. The combined organic phase was dried over MgSO4 and concentrated under reduced pressure. The residue was purified by flash chromatography (CombiFlash® Companion System®, with RediSep® silica gel column, EtOAc/MeOH (1% NH3)=100:0->80:20) to afford the title compound as a white crystalline powder (tR 3.40 min (conditions 3), MH+=403.3, 1H-NMR in DMSO-d6: 8.81 (d, 1H), 8.35-8.28 (m, 2H); 8.05 (d, 1H); 7.95-7.88 (m, 2H), 7.76 (d, 1H); 7.72 (s, 1H); 7.49 (d, 1H); 7.46-7.40 (m, 1H); 5.03 (q, 1H); 4.92 (t, 1H); 4.15 (t, 2H); 3.72 (q, 2H); 2.83 (d, 3H)).

후처리

  1. customprecipitated as an oil
  2. extractionextracted with DCM
  3. dry with materialThe combined organic phase was dried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by flash chromatography (CombiFlash® Companion System®, with RediSep® silica gel column, EtOAc/MeOH (1% NH3)=100:0->80:20)

출처 및 근거

ORD 기록
ord-a673924a7c5f49b68b6f95decd7fae48
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822468B2

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