Sodium Carbonate → HCID 56597463, 화합물

HRID 2174952노트

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HRID 2174952 반응식
[C:1]([N:3]=[C:4]1[N:19]([CH3:20])[C:7]2[CH:8]=[N:9][C:10]3[CH:11]=[CH:12][C:13](B(O)O)=[CH:14][C:15]=3[C:6]=2[N:5]1[C:21]1[CH:26]=[CH:25][C:24]([C:27]([C:30]#[N:31])([CH3:29])[CH3:28])=[CH:23][CH:22]=1)#[N:2].Br[C:33]1[CH:34]=[C:35]([NH:41][S:42]([C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)(=[O:44])=[O:43])[C:36]([O:39][CH3:40])=[N:37][CH:38]=1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C>[C:1]([N:3]=[C:4]1[N:19]([CH3:20])[C:7]2[CH:8]=[N:9][C:10]3[CH:11]=[CH:12][C:13]([C:33]4[CH:34]=[C:35]([NH:41][S:42]([C:45]5[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=5)(=[O:44])=[O:43])[C:36]([O:39][CH3:40])=[N:37][CH:38]=4)=[CH:14][C:15]=3[C:6]=2[N:5]1[C:21]1[CH:26]=[CH:25][C:24]([C:27]([C:30]#[N:31])([CH3:29])[CH3:28])=[CH:23][CH:22]=1)#[N:2]

참가 물질

5

반응물 3

HCID 10340Sodium CarbonateHCID 59859943HCID 59859943, 화합물HCID 86683444HCID 86683444, 화합물

생성물 1

HCID 56597463HCID 56597463, 화합물

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
111 °C

실험 절차

To the stirred solution (2-(cyanoimino)-1-(4-(2-cyanopropan-2-yl)phenyl)-3-methyl-2,3-dihydro-1H-imidazo[4,5-c]quinolin-8-yl)boronic acid (0.390 mmol) in dry DMF (5 ml) was added N-(5-bromo-2-methoxypyridin-3-yl)benzenesulfonamide (0.39 mmol) followed by catalyst palladium dichlorobis triphenylphosphine (0.039 mmol). Saturated solution of sodium carbonate (0.780 mmol) was added to it and the resulting solution was heated at 111° C. for 8 minutes in microwave. Solvent was removed and the crude material was extracted with EtOAc, washed with brine several times and dried over anhydrous Na2SO4. The solvent was evaporated and the crude solid was purified (silica gel column, CHCl3/MeOH as eluent) to obtain the title compound. 1H NMR (300 MHz, DMSO-d6): δ 10.01 (s, 1H), 9.23 (s, 1H), 8.20 (d, J=8.7 Hz, 1H), 7.88 (s, 4H), 7.84 (m, 1H), 7.70 (m, 4H), 7.56 (m, 3H), 6.83 (s, 1H), 3.92 (s, 3H), 3.58 (s, 3H), 1.81 (s, 6H); MS (m/z): 629 (M+1)+.

후처리

  1. customSolvent was removed
  2. extractionthe crude material was extracted with EtOAc
  3. washwashed with brine several times
  4. dry with materialdried over anhydrous Na2SO4
  5. customThe solvent was evaporated
  6. customthe crude solid was purified (silica gel column, CHCl3/MeOH as eluent)

출처 및 근거

ORD 기록
ord-a71377fb55b44619a289c61bb2a88f44
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09062046B2

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