2-Pyridinemethanamine → HCID 57541262, 화합물

HRID 421746노트

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HRID 421746 반응식
[NH2:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1.[Cl:9][C:10]1[CH:11]=[C:12]2[C:20](=[O:21])[C:19]3[CH:22]=[C:23]([CH2:26][S:27](N(C)C4C=CC=CC=4)(=[O:29])=[O:28])[CH:24]=[CH:25][C:18]=3[CH:17]=[CH:16][C:13]2=[N:14][CH:15]=1.C(=O)([O-])O.[Na+]>CN1CCCC1=O>[Cl:9][C:10]1[CH:11]=[C:12]2[C:20](=[O:21])[C:19]3[CH:22]=[C:23]([CH2:26][S:27]([NH:1][CH2:2][C:3]4[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=4)(=[O:29])=[O:28])[CH:24]=[CH:25][C:18]=3[CH:17]=[CH:16][C:13]2=[N:14][CH:15]=1

참가 물질

5

반응물 3

HCID 195092-PyridinemethanamineHCID 516892Sodium BicarbonateHCID 57541245HCID 57541245, 화합물

생성물 1

HCID 57541262HCID 57541262, 화합물

시약·촉매·용매 1

HCID 13387N-methyl-2-pyrrolidone용매

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온도
132.5 °C

실험 절차

2-Aminomethylpyridine (55.9 ml, 546 mmol) was added to a solution of 1-(3-chloro-5-oxo-5H-benzo[4,5]cyclohepta[1,2-b]pyridin-7-yl)-N-methyl-N-phenylmethanesulfonamide (51.6 g, 121 mmol) in N-methyl-2-pyrrolidinone (1214 ml) at room temperature. The solution was then heated to 130-135° C. for 2 h in a pre-warmed oil bath. The solution was then cooled to room temperature and poured into aqueous sodium hydrogen carbonate (saturated, 3.0 L) and 500 mL ice-water and extracted with ethyl acetate (3×500 mL). The combined organics were dried over anhydrous Na2 SO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (EtOAc/Hexanes gradient) to afford the title compound as a yellow solid. 1H NMR (600 MHz, DMSO-D6) δ 8.99 (d, 1H); 8.47 (d, 1H); 8.46 (m, 1H); 8.16 (d, 1H); 7.81 (m, 3H); 7.76 (m, 1H); 7.49 (d, 1H); 7.38 (d, 1H); 7.32 (d, 1H); 7.25 (m, 1H); 4.63 (s, 2H); 4.22 (d, 2H). LRMS (APCI) calculated for C21H17ClN3O3S [M+H]+, 426.1; found 426.0.

후처리

  1. temperatureThe solution was then cooled to room temperature
  2. extractionextracted with ethyl acetate (3×500 mL)
  3. customThe combined organics were dried over anhydrous Na2 SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel (EtOAc/Hexanes gradient)

출처 및 근거

ORD 기록
ord-1971cbdb529c4598931cd284dbf735ea
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08101603B2

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