Sodium Carbonate → N-[(4,6-Dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-6-(1H-indazol-6-yl)-1-(1-methylethyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxamide

HRID 476005

반응식

HRID 476005 반응식
Cl[C:2]1[CH:3]=[C:4]([C:14]([NH:16][CH2:17][C:18]2[C:19](=[O:26])[NH:20][C:21]([CH3:25])=[CH:22][C:23]=2[CH3:24])=[O:15])[C:5]2[CH:10]=[N:9][N:8]([CH:11]([CH3:13])[CH3:12])[C:6]=2[N:7]=1.CC1(C)C(C)(C)OB([C:35]2[CH:43]=[C:42]3[C:38]([CH:39]=[N:40][NH:41]3)=[CH:37][CH:36]=2)O1.C(=O)([O-])[O-].[Na+].[Na+]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CS(C)=O>[CH3:24][C:23]1[CH:22]=[C:21]([CH3:25])[NH:20][C:19](=[O:26])[C:18]=1[CH2:17][NH:16][C:14]([C:4]1[C:5]2[CH:10]=[N:9][N:8]([CH:11]([CH3:13])[CH3:12])[C:6]=2[N:7]=[C:2]([C:35]2[CH:43]=[C:42]3[C:38]([CH:39]=[N:40][NH:41]3)=[CH:37][CH:36]=2)[CH:3]=1)=[O:15]

참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 441192506-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazoleHCID 565974256-Chloro-N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1-(1-methylethyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxamide

생성물 1

HCID 56598542N-[(4,6-Dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-6-(1H-indazol-6-yl)-1-(1-methylethyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxamide

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물촉매HCID 679Dimethyl Sulfoxide용매

실험 절차

The title compound was prepared in the same manner as described in example 74 from 6-chloro-N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1-(1-methylethyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxamide (70 mg, 0.187 mmol), 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole (59.4 mg, 0.243 mmol), DMSO (1.5 mL), sodium carbonate (0.281 mL, 0.562 mmol), and bis(triphenylphosphine)palladium(II) chloride (10.51 mg, 0.015 mmol). The final product was collected as 55 mg (65%). LCMS E-S (M+H)=456.0 1H NMR (400 MHz, DMSO-d6) δ ppm 1.49-1.65 (m, J=6.4 Hz, 6H), 2.14 (s, 3H), 2.23 (s, 3H), 4.43 (d, J=4.6 Hz, 2H), 5.36 (quin, J=6.7 Hz, 1H), 5.87-5.97 (m, 1H), 7.52-7.72 (m, 2H) 7.92 (d, J=8.6 Hz, 1H), 8.08 (d, J=8.6 Hz, 1H), 8.16 (s, 1H), 8.26 (s, 1H), 8.37-8.49 (m, 2H), 8.96-9.14 (m, 1H), 11.59 (br. s., 1H).

후처리

  1. customThe final product was collected as 55 mg (65%)

출처 및 근거

ORD 기록
ord-27b9329a656044b685b04352184b958c
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08637509B2

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