Water → HCID 86661686, 화합물

HRID 1262187

반응식

HRID 1262187 반응식
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

참가 물질

9

반응물 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

생성물 1

HCID 86661686HCID 86661686, 화합물수율 100%

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 6228Dimethylformamide용매HCID 312751,4-Dioxane용매

반응 조건

온도
90 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-909aed71747644fbaa02f05ad3e6252f
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08471005B2

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