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Methanone, (3-aminophenyl)phenyl- → HCID 10178531, 화합물

HRID 1392986
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HRID 1392986 반응식
CS[C:3]1[N:8]=[C:7]([C:9]2[N:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]3=[N:11][CH:10]=2)[CH:6]=[CH:5][N:4]=1.[NH2:18][C:19]1[CH:20]=[C:21]([CH:30]=[CH:31][CH:32]=1)[C:22]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:23].[H-].[Na+]>CN(C)C=O>[C:22]([C:21]1[CH:20]=[C:19]([CH:32]=[CH:31][CH:30]=1)[NH:18][C:3]1[N:8]=[C:7]([C:9]2[N:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]3=[N:11][CH:10]=2)[CH:6]=[CH:5][N:4]=1)(=[O:23])[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 17817Methanone, (3-aminophenyl)phenyl-HCID 24758Sodium hydrideHCID 20751408HCID 20751408, 화합물

생성물 1

HCID 10178531HCID 10178531, 화합물수율 12%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
130 °C

실험 절차

To a solution of 2-methylsulfanyl-4-(imidazo-[1,2-a]pyridin-3-yl)pyrimidine (0.146 g, 0.60 mmol) and 3-aminobenzophenone (0.238 g, 1.21 mmol) in N,N-dimethylformamide (2.5 mL) was added sodium hydride (0.061 g, 1.52 mmol) and the mixture was heated at 130° C. for 4 hours. The mixture was allowed to cool to room temperature and the solvent was removed. The residue was dissolved in water and the resulting solid was washed with water and chloroform. The organic phase was dried over MgSO4 and the solvent was evaporated. The crude product was purified by column chromatography on silica gel using chloroform/ethanol, 9:1, as the eluent affording 0.028 g (12% yield) of the title compound as a yellow solid: mp (decomp.) 237-246° C.; MS (TSP) m/z 392 (M+1); 1H NMR (400 MHz, DMSO-d6) δ 10.25 (d, J=6.3 Hz, 1 H), 10.15 (s, 1 H), 8.74 (s, 1 H), 8.55 (d, J=5.4 Hz, 1 H), 8.29 (s, 1 H), 8.25 (d, J=8.1 Hz, 1 H), 7.87 (m, 3 H), 7.78 (t, J=7.4 Hz, 1 H), 7.67 (m, 2 H), 7.60 (m, 2 H), 7.55 (d, J=5.4 Hz, 1 H), 7.44 (d, J=7.5 Hz, 1 H), 7.20 (m, 1 H).

후처리

  1. temperatureto cool to room temperature
  2. customthe solvent was removed
  3. dissolutionThe residue was dissolved in water
  4. washthe resulting solid was washed with water and chloroform
  5. dry with materialThe organic phase was dried over MgSO4
  6. customthe solvent was evaporated
  7. customThe crude product was purified by column chromatography on silica gel

출처 및 근거

ORD 기록
ord-70b74bc18fd54b1eb2c29c9bdfb7a8c9
출처 데이터셋
uspto-grants-2008_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07345050B2

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