Water → HCID 86661686、化合物

HRID 1262187

反応式

HRID 1262187 の反応式
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.Br[C:21]1[N:29]2[C:24]([CH:25]=[N:26][C:27]([NH:30][C:31]3[CH:36]=[CH:35][C:34]([N:37]4[CH2:42][CH2:41][N:40]([CH3:43])[CH2:39][CH2:38]4)=[CH:33][CH:32]=3)=[N:28]2)=[CH:23][CH:22]=1.B([C:47]1[CH:52]=[CH:51][C:50]([CH2:53][N:54]2[CH2:59][CH2:58][S:57](=[O:61])(=[O:60])[CH2:56][CH2:55]2)=[CH:49][CH:48]=1)(O)O.C(=O)([O-])[O-].[Na+].[Na+].O>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CN(C)C=O>[O:61]=[S:57]1(=[O:60])[CH2:58][CH2:59][N:54]([CH2:53][C:50]2[CH:51]=[CH:52][C:47]([C:21]3[N:29]4[C:24]([CH:25]=[N:26][C:27]([NH:30][C:31]5[CH:32]=[CH:33][C:34]([N:37]6[CH2:42][CH2:41][N:40]([CH3:43])[CH2:39][CH2:38]6)=[CH:35][CH:36]=5)=[N:28]4)=[CH:23][CH:22]=3)=[CH:48][CH:49]=2)[CH2:55][CH2:56]1

参加物

9

反応物 5

HCID 962WaterHCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 54970580(4-((1,1-Dioxidothiomorpholino)methyl)phenyl)boronic acidHCID 66711200(7-Bromo-pyrrolo[2,1-f][1,2,4]triazin-2-yl)-[4-(4-methyl-piperazin-1-yl)-phenyl]-amine

生成物 1

HCID 86661686HCID 86661686、化合物収率 100%

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 6228Dimethylformamide溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
90 °C

実験手順

Palladium acetate (25.5 mg, 0.114 mmol) and triphenylphosphine (65.6 mg, 0.250 mmol) were dissolved in 1,4-dioxane (2.00 mL) and the mixture was purged with nitrogen for 10 minutes. (7-Bromo-pyrrolo[2,1-f][1,2,4]triazin-2-yl)-[4-(4-methyl-piperazin-1-yl)-phenyl]-amine (110 mg, 0.284 mmol), 4-[(4-boronophenyl)methyl]-thiomorpholine 1,1-dioxide (306 mg, 1.14 mmol), N,N-dimethylformamide (2.00 mL) and 1.50 M sodium carbonate in water (0.379 mL, 0.568 mmol) were added. The reaction mixture was heated at 90° C. overnight and then partitioned between water (50 mL) and dichloromethane (50 mL). The organic layer was washed with water (50 mL) and brine (25 mL) and then dried over Na2SO4. Purification by silica gel chromatography using a gradient of 0-10% MeOH/DCM as the eluting solvent to obtain the title compound as a yellow-brown foam (151 mg, 100%). LCMS (m/e) 532 (M+H); 1H-NMR (CDCl3, 400 MHz) δ 8.69 (s, 1H), 8.13 (d, 2H, J=7.4 Hz), 7.54 (d, 2H, J=7.8 Hz), 7.41 (d, 2H, J=7.8 Hz), 7.02-6.90 (m, 3H), 6.84-6.78 (m, 1H), 6.70-6.62 (m, 1H), 3.73 (s, 2H), 3.23-3.15 (m, 4H), 3.13-3.00 (m, 8H), 2.66-2.57 (m, 4H), 2.38 (s, 3H).

後処理

  1. customthe mixture was purged with nitrogen for 10 minutes
  2. custompartitioned between water (50 mL) and dichloromethane (50 mL)
  3. washThe organic layer was washed with water (50 mL) and brine (25 mL)
  4. dry with materialdried over Na2SO4
  5. customPurification by silica gel chromatography

出典と根拠

ORDレコード
ord-909aed71747644fbaa02f05ad3e6252f
出典データセット
uspto-grants-2013_06
特許番号
US08471005B2

関連ノート

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