Hydrochloric Acid → methyl 2-(1-methyl-3-phenyl-4-(trifluoromethyl)-1H-pyrazolo[3,4-b]pyridin-6-ylamino)acetate

HRID 402480

반응식

HRID 402480 반응식
Br[C:2]1[N:7]=[C:6]2[N:8]([CH3:17])[N:9]=[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:5]2=[C:4]([C:18]([F:21])([F:20])[F:19])[CH:3]=1.C([O-])([O-])=O.[Na+].[Na+].Cl.[CH3:29][O:30][C:31](=[O:34])[CH2:32][NH2:33]>CN(C=O)C>[CH3:17][N:8]1[C:6]2=[N:7][C:2]([NH:33][CH2:32][C:31]([O:30][CH3:29])=[O:34])=[CH:3][C:4]([C:18]([F:21])([F:20])[F:19])=[C:5]2[C:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[N:9]1

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 69221Glycine methyl esterHCID 866720496-bromo-1-methyl-3-phenyl-4-(trifluoromethyl)-1H-pyrazolo[3,4-b]pyridine

생성물 1

HCID 67209395methyl 2-(1-methyl-3-phenyl-4-(trifluoromethyl)-1H-pyrazolo[3,4-b]pyridin-6-ylamino)acetate수율 32%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
100 °C

실험 절차

To a stirred mixture of 6-bromo-1-methyl-3-phenyl-4-(trifluoromethyl)-1H-pyrazolo[3,4-b]pyridine (0.15 g, 0.422 mmol) and Na2CO3 (0.135 g, 1.267 mmol) in dry DMF (6.0 mL), glycine methylester×HCl (0.08 g, 0.633 mmol) was added at it and heated to 100° C. for 6 h. The reaction mixture was cooled to it and poured into rapidly stirred ice cold water. The crude compound was extracted with EtOAc and purified by column chromatography (eluent: 10% EtOAc in hexane) to yield the title compound as a colorless solid (0.05 g, 32%). [1H-NMR (CDCl3, 300 MHz) δ 7.55-7.38 (m, 5H), 6.68 (s, 1H), 5.42 (t, 1H), 4.32 (d, 2H), 4.05 (s, 3H), 3.75 (s, 3H); LCMS RtC=0.469 min; [M+H]+=364.8]

후처리

  1. additionwas added at it
  2. temperatureThe reaction mixture was cooled to it
  3. additionpoured into rapidly stirred ice cold water
  4. extractionThe crude compound was extracted with EtOAc
  5. custompurified by column chromatography (eluent: 10% EtOAc in hexane)

출처 및 근거

ORD 기록
ord-929f906dc1694cd1887310cfeb9ecb8a
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08742106B2

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