Hydrochloric Acid → 1-(3-chloro-4-fluorophenyl)-6-[4-iodophenyl]-3-(trifluoromethyl)-1,4,5,6-tetrahydro-7H-pyrazolo[3,4-c]pyridin-7-one

HRID 890513노트

반응식

HRID 890513 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][NH2:10])[CH:5]=[CH:6][C:7]=1[F:8].[I:11][C:12]1[CH:17]=[CH:16][C:15]([N:18]2[CH2:23][CH2:22][CH:21]([C:24](=O)[C:25]([F:28])([F:27])[F:26])[C:20](=O)[C:19]2=[O:31])=[CH:14][CH:13]=1.C(O)C.Cl>C(OC(=O)C)C>[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[C:20]3[C:19](=[O:31])[N:18]([C:15]4[CH:16]=[CH:17][C:12]([I:11])=[CH:13][CH:14]=4)[CH2:23][CH2:22][C:21]=3[C:24]([C:25]([F:28])([F:26])[F:27])=[N:10]2)[CH:5]=[CH:6][C:7]=1[F:8]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 27365753-Chloro-4-fluorophenylhydrazineHCID 222404772,3-Piperidinedione, 1-(4-iodophenyl)-4-(2,2,2-trifluoroacetyl)-

생성물 1

HCID 222404461-(3-chloro-4-fluorophenyl)-6-[4-iodophenyl]-3-(trifluoromethyl)-1,4,5,6-tetrahydro-7H-pyrazolo[3,4-c]pyridin-7-one수율 75%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

Part A. 3-chloro-4-fluorophenyl hydrazine (5.00 g, 31.14 mmol) and 1-(4-iodophenyl)-4-(trifluoroacetyl)-2,3-piperidinedione (12.8 g, 31.14 mmol) were added together with 120 mL of ethanol and 4 mL of hydrochloric acid (12 M). The mixture was stirred at reflux under N2 for overnight. The reaction was cooled down to rt. The solvents were removed, and the residue was dissolved in EtOAc (200 mL) and washed with water (100 mL×2) and brine (50 mL). It was then dried over Na2SO4 and concentrated. The residue was purified via flash chromatography on silica gel using 4:1 hexane:ethylacetate to give 1-(3-chloro-4-fluorophenyl)-6-[4-iodophenyl]-3-(trifluoromethyl)-1,4,5,6-tetrahydro-7H-pyrazolo[3,4-c]pyridine-7-one as a brown solid (12.5 g, 75% yield). LRMS (AP+): 536.1 (M+H)+. 1H NMR (CDCl3) δ 7.72 (d, 2H), 7.67–7.64 (m, 1H), 7.49–7.44 (m, 1H), 7.19 (t, 3H), 7.06 (d, 2H), 4.12 (t, 2H), 3.17 (t, 2H).

후처리

  1. temperatureat reflux under N2 for overnight
  2. customThe solvents were removed
  3. dissolutionthe residue was dissolved in EtOAc (200 mL)
  4. washwashed with water (100 mL×2) and brine (50 mL)
  5. dry with materialIt was then dried over Na2SO4
  6. concentrationconcentrated
  7. customThe residue was purified via flash chromatography on silica gel using 4:1 hexane

출처 및 근거

ORD 기록
ord-9e532b8703754bc4a9097fb9017d4801
출처 데이터셋
uspto-grants-2006_02
특허 번호
US06995172B2

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