Water → 6-{4-[(Dimethylamino)sulfonyl]phenyl}-N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1-(1-methylethyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxamide

HRID 1522378노트

반응식

HRID 1522378 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.[CH3:27][N:28]([CH3:41])[S:29]([C:32]1[CH:37]=[CH:36][C:35](B(O)O)=[CH:34][CH:33]=1)(=[O:31])=[O:30].C(=O)(O)[O-].[Na+].O>COCCOC.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(Cl)Cl>[CH3:27][N:28]([CH3:41])[S:29]([C:32]1[CH:33]=[CH:34][C:35]([C:2]2[CH:3]=[C:4]([C:14]([NH:16][CH2:17][C:18]3[C:19](=[O:26])[NH:20][C:21]([CH3:25])=[CH:22][C:23]=3[CH3:24])=[O:15])[C:5]3[CH:10]=[N:9][N:8]([CH:11]([CH3:13])[CH3:12])[C:6]=3[N:7]=2)=[CH:36][CH:37]=1)(=[O:30])=[O:31]

참가 물질

7

반응물 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 441193284-(N,N-Dimethylsulphonamido)benzeneboronic acidHCID 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 565972916-{4-[(Dimethylamino)sulfonyl]phenyl}-N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1-(1-methylethyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxamide수율 57.4%

시약·촉매·용매 2

HCID 178418807HCID 178418807, 화합물촉매HCID 18180031Water 1,2-dimethoxyethane용매

반응 조건

온도
110 °C

실험 절차

In a 25 mL sealable tube under nitrogen were combined 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 (85 mg, 0.23 mmol) and {4-[(dimethylamino)sulfonyl]phenyl}boronic acid (104 mg, 0.46 mmol) in DME/water (3 ml:1 ml). PdCl2(dppf)-CH2Cl2 adduct (9.3 mg, 0.011 mmol) was added and the resulting mixture was degassed with nitrogen for 10 min. Sodium bicarbonate (57.3 mg, 0.68 mmol) was added and the insoluble light brown mixture was heated in an oil bath at 110° C. for 3 hrs. After cooling, 2 mL of water was added to the black mixture and solids that precipitated were filtered. DMF was added along with a few drops of water and solids were filtered. DCM/MeOH (1:1) was added to the grey solids and they were filtered and dried to afford the title compound (69 mg, 57%) as a grayish solid. LCMS E-S (M+H)=523.2. 1H NMR (400 MHz, DMSO-d6) δ ppm 11.59 (br. s., 1 H), 9.01 (br. s., 1 H), 8.51 (m, J=8.34 Hz, 2 H), 8.44 (s, 1 H), 8.27 (s, 1 H), 7.93 (m, J=8.34 Hz, 2 H), 5.91 (s, 1 H), 5.36 (dt, J=13.14, 6.57 Hz, 1 H), 4.43 (d, J=4.55 Hz, 2 H), 2.66 (s, 6 H), 2.23 (s, 3 H), 2.13 (s, 3 H), 1.56 (d, J=6.57 Hz, 6 H).

후처리

  1. customIn a 25 mL sealable tube under nitrogen were combined
  2. customthe resulting mixture was degassed with nitrogen for 10 min
  3. temperatureAfter cooling
  4. customthat precipitated
  5. filtrationwere filtered
  6. additionDMF was added along with a few drops of water and solids
  7. filtrationwere filtered
  8. additionDCM/MeOH (1:1) was added to the grey solids and they
  9. filtrationwere filtered
  10. customdried

출처 및 근거

ORD 기록
ord-0dd7a69182354b218bc7bde7e1ecfd0f
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09073924B2

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