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Hydrochloric Acid → 1-(4-(5-(2,6-difluorophenyl)-1H-indol-3-yl)-6-methoxypyrimidin-2-yl)piperidin-4-amine

HRID 1529420
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HRID 1529420 반응식
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][CH:13]=[C:12]2[C:18]1[CH:23]=[C:22]([O:24][CH3:25])[N:21]=[C:20]([N:26]2[CH2:31][CH2:30][CH:29]([NH:32]C(=O)OC(C)(C)C)[CH2:28][CH2:27]2)[N:19]=1.Cl>O1CCOCC1>[F:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[C:3]=1[C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][CH:13]=[C:12]2[C:18]1[CH:23]=[C:22]([O:24][CH3:25])[N:21]=[C:20]([N:26]2[CH2:31][CH2:30][CH:29]([NH2:32])[CH2:28][CH2:27]2)[N:19]=1
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참가 물질

4

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HCID 313Hydrochloric AcidHCID 67976781tert-butyl (1-(4-(5-(2,6-difluorophenyl)-1H-indol-3-yl)-6-methoxypyrimidin-2-yl)piperidin-4-yl)carbamate

생성물 1

HCID 679597241-(4-(5-(2,6-difluorophenyl)-1H-indol-3-yl)-6-methoxypyrimidin-2-yl)piperidin-4-amine수율 25%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매2회

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온도
90 °C

실험 절차

To solution of tert-butyl (1-(4-(5-(2,6-difluorophenyl)-1H-indol-3-yl)-6-methoxypyrimidin-2-yl)piperidin-4-yl)carbamate (0.1 g, 0.187 mmol) in dioxane (2 mL) was added HCl in dioxane (2 mL) and the mixture was heated at 90° C. for overnight. The reaction was quenched with aq.NaHCO3 and extracted with EtOAc. The organic layer was dried (Na2SO4), filtered and concentrated. The residue was purified with basic alumina column chromatography. (eluting in 1% MeOH in CHCl3) to give 1-(4-(5-(2,6-difluorophenyl)-1H-indol-3-yl)-6-methoxypyrimidin-2-yl)piperidin-4-amine (20 mg, 25%). MS (ESI, pos. ion) m/z: 436.1 (M+1); 1H-NMR (DMSO-d6, 400 MHz): δ ppm 11.84 (brs, 1H), 8.58 (s, 1H), 8.29 (s, 1H), 7.56 (d, 1 H, J=8.4 Hz), 7.47-7.43 (m, 1H), 7.19-7.27 (m, 3H), 6.54 (s, 1H), 4.7 (d, J=12 Hz, 2H), 3.8 (s, 3H), 3.0 (t, J=12 Hz, 2H), 1.85-1.89 (m, 3H), 1.38-1.40 (m, 2H).

후처리

  1. customThe reaction was quenched with aq
  2. extractionNaHCO3 and extracted with EtOAc
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified with basic alumina column chromatography
  7. wash(eluting in 1% MeOH in CHCl3)

출처 및 근거

ORD 기록
ord-9efb8c4dd5144be5ba12628ced47ce8d
출처 데이터셋
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09090593B2

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