Water → HCID 56598812、化合物

HRID 476020ノート

反応式

HRID 476020 の反応式
Cl[C:2]1[CH:3]=[C:4]([C:15]([NH:17][CH2:18][C:19]2[C:20](=[O:27])[NH:21][C:22]([CH3:26])=[CH:23][C:24]=2[CH3:25])=[O:16])[C:5]2[C:10]([CH3:11])=[N:9][N:8]([CH:12]([CH3:14])[CH3:13])[C:6]=2[N:7]=1.[CH3:28][NH:29][S:30]([C:33]1[CH:38]=[CH:37][C:36](B(O)O)=[CH:35][CH:34]=1)(=[O:32])=[O:31].C(=O)(O)[O-].[Na+].O>COCCOC.O.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>[CH3:25][C:24]1[CH:23]=[C:22]([CH3:26])[NH:21][C:20](=[O:27])[C:19]=1[CH2:18][NH:17][C:15]([C:4]1[C:5]2[C:10]([CH3:11])=[N:9][N:8]([CH:12]([CH3:14])[CH3:13])[C:6]=2[N:7]=[C:2]([C:36]2[CH:35]=[CH:34][C:33]([S:30]([NH:29][CH3:28])(=[O:31])=[O:32])=[CH:38][CH:37]=2)[CH:3]=1)=[O:16]

参加物

7

反応物 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 441187634-((Methylamino)sulphonyl)benzene boronic acidHCID 565974266-Chloro-N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-3-methyl-1-(1-methylethyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxamide

生成物 1

HCID 56598812HCID 56598812、化合物

試薬・触媒・溶媒 2

HCID 178418476HCID 178418476、化合物触媒HCID 18180031Water 1,2-dimethoxyethane溶媒

実験手順

6-Chloro-N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-3-methyl-1-(1-methylethyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxamide (80 mg, 0.21 mmol), {4-[(methylamino)sulfonyl]phenyl}boronic acid (66.5 mg, 0.31 mmol) and bis(triphenylphosphine)palladium(II) chloride (8.4 mg, 0.01 mmol) were suspended in DME/water (4 mL, 3:1) and stirred for 10 min under nitrogen at room temperature. Sodium bicarbonate (52 mg, 0.62 mmol) was added and the heterogenous mixture was irradiated (microwave) at 150° C. for 30 min. After cooling to room temperature, water was added to the black mixture, and the contents were vacuum filtered. The crude product was dissolved in DCM/MeOH (1:1) and preabsorbed onto silica gel. The product was purified by silica gel chromatography (eluent: DCM/MeOH/NH4OH, gradient of 0 to 90:10:1). The light beige solid that was collected was suspended in EtOH, sonicated, and filtered. The solid was then air-dried for 15 min, and then in vacuum oven overnight. The final product was collected as 77 mg (70%). LCMS E-S (M+H)=523.2 1H NMR (400 MHz, DMSO-d6) δ ppm 11.54 (br. s., 1H) 8.78 (t, J=5.05 Hz, 1H) 8.43 (m, J=8.59 Hz, 2H) 7.93 (m, J=8.59 Hz, 2H) 7.78 (s, 1H) 7.58 (br. s., 1H) 5.89 (s, 1H) 5.29 (quin, J=6.63 Hz, 1H) 4.40 (d, J=4.80 Hz, 2H) 2.46 (d, J=1.26 Hz, 6H) 2.25 (s, 3H) 2.12 (s, 3H) 1.52 (s, 3H) 1.51 (s, 3H).

後処理

  1. customthe heterogenous mixture was irradiated (microwave) at 150° C. for 30 min
  2. temperatureAfter cooling to room temperature
  3. filtrationfiltered
  4. dissolutionThe crude product was dissolved in DCM/MeOH (1:1)
  5. custompreabsorbed onto silica gel
  6. customThe product was purified by silica gel chromatography (eluent: DCM/MeOH/NH4OH, gradient of 0 to 90:10:1)
  7. customThe light beige solid that was collected
  8. customsonicated
  9. filtrationfiltered
  10. customThe solid was then air-dried for 15 min
  11. customin vacuum oven overnight
  12. customThe final product was collected as 77 mg (70%)

出典と根拠

ORDレコード
ord-d8545005fc9742fea726d144f4a2b418
出典データセット
uspto-grants-2014_01
特許番号
US08637509B2

反応ノート

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