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Hydrochloric Acid → (Rac)-2-(4-{3-[1-(6-fluoro-1-methyl-1h-indazol-5-yl)-ethyl]-imidazo[1,2-b]pyridazin-6-yl}-pyrazol-1-yl)-ethanol

HRID 69282
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인쇄 미리보기

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HRID 69282 반응식
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][N:8]2[CH3:11])=[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.CCOC(C)=O>[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][N:8]2[CH3:11])=[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]
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참가 물질

6

반응물 2

HCID 313Hydrochloric AcidHCID 69077766HCID 69077766, 화합물

생성물 1

HCID 57917348(Rac)-2-(4-{3-[1-(6-fluoro-1-methyl-1h-indazol-5-yl)-ethyl]-imidazo[1,2-b]pyridazin-6-yl}-pyrazol-1-yl)-ethanol

시약·촉매·용매 3

HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매
HCID 31275
1,4-Dioxane
용매

실험 절차

(rac)-3-[1-(6-Fluoro-1-methyl-1H-indazol-5-yl)-ethyl]-6-{1-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-1H-pyrazol-4-yl}-imidazo[1,2-b]pyridazine (Stage 279.1, 250 mg, 0.511 mmol) was dissolved in DCM (5 mL). HCl in dioxane (4 N, 0.5 mL) was added and the RM was stirred 1 h at rt. It was then diluted with EtOAc and washed with a saturated NaHCO3 sol. The aqueous phase was extracted twice with EtOAc. The combined organics were washed with brine, dried over Na2SO4, filtered and evaporated. The residue was purified by preparative HPLC with acetonitrile and water (+0.1% TFA) to afford the title compound as a white solid (tR 0.98 min (conditions 2), MH+=406, 1H-NMR in DMSO-d6: 8.39 (s, 1H); 8.07 (d, 2H); 8.01 (d, 1H); 7.69 (s, 1H); 7.61 (s, 1H); 7.51 (d, 1H); 7.47 (d, 1H); 7.23 (d, 1H); 4.95 (t, 1H); 4.76 (q, 1H); 4.18 (t, 2H); 3.78 (s, 3H); 3.75 (q, 2H); 1.79 (d, 3H)).

후처리

  1. washwashed with a saturated NaHCO3 sol. The aqueous phase
  2. extractionwas extracted twice with EtOAc
  3. washThe combined organics were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by preparative HPLC with acetonitrile and water (+0.1% TFA)

출처 및 근거

ORD 기록
ord-bce8da3f8332470798f0becf2d4df00b
출처 데이터셋
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08822468B2

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