Hydrochloric Acid → 4-Chloro-5-(4-chloro-phenyl)-6-(2,4-dichloro-phenyl)-1-phenyl-1H-pyrazolo[3,4-b]pyridine

HRID 1693498

반응식

HRID 1693498 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9](N)=[C:10]3[CH:24]=[N:23][N:22]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[C:11]3=[N:12][C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=2[Cl:21])=[CH:4][CH:3]=1.[ClH:32].N([O-])=O.[Na+].C([O-])(O)=O.[Na+]>CC#N>[Cl:32][C:9]1[C:8]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)=[C:13]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=2[Cl:21])[N:12]=[C:11]2[N:22]([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[N:23]=[CH:24][C:10]=12

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 116196625-(4-chloro-phenyl)-6-(2,4-dichlorophenyl)-1-phenyl-1H-pyrazolo[3,4-b]pyridin-4-ylamineHCID 23668193Sodium Nitrite

생성물 1

HCID 116127804-Chloro-5-(4-chloro-phenyl)-6-(2,4-dichloro-phenyl)-1-phenyl-1H-pyrazolo[3,4-b]pyridine수율 24%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

To a solution of 5-(4-chloro-phenyl)-6-(2,4-dichlorophenyl)-1-phenyl-1H-pyrazolo[3,4-b]pyridin-4-ylamine (16 mg, 0.034 mmol) in CH3CN (0.4 mL) is added cone. HCl (0.8 mL). NaNO2 (20 mg, 0.29 mmol) is added into the mixture at 0° C. After the addition, the mixture is warmed up to room temperature and stirred for 24 h. The mixture is then neutralized to pH˜7 by adding saturated aqueous NaHCO3 and extracted with EtOAc (3×3 mL). The combined organic layers are concentrated and purified by preparative thin layer chromatography to provide the titled compound as a white solid (4 mg, 24%). 1H NMR (CDCl3) δ(ppm) 8.35(s, 1H), 8.28 (d, 2H), 7.50 (t, 2H), 7.27-7.37(m, 2H), 7.24-7.26 (m, 2H), 7.07-7.16 (m, 4H); HPLC-MS calculated for C24H13Cl4N3 (M+1+): 484.0. Found: 484.1.

후처리

  1. additionAfter the addition
  2. extractionextracted with EtOAc (3×3 mL)
  3. concentrationThe combined organic layers are concentrated
  4. custompurified by preparative thin layer chromatography

출처 및 근거

ORD 기록
ord-aa9701aa7cbf49c5ae20ffa04d3829b5
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08158634B2

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