Benzoyl chloride → 2-benzamido-N-benzylisonicotinamide

HRID 714313노트

반응식

HRID 714313 반응식
[NH2:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][N:17]=1)[C:5]([NH:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:6].CN(C1C=CC=CN=1)C.C(N(CC)C(C)C)(C)C.[C:36](Cl)(=[O:43])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>O1CCCC1.C(OCC)(=O)C>[C:36]([NH:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][N:17]=1)[C:5]([NH:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:6])(=[O:43])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

참가 물질

7

반응물 4

HCID 7412Benzoyl chlorideHCID 218852-DimethylaminopyridineHCID 81531DiisopropylethylamineHCID 187528972-amino-N-benzylisonicotinamide

생성물 1

HCID 671538562-benzamido-N-benzylisonicotinamide수율 15%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 2-amino-N-benzylisonicotinamide (0.23 g, 0.43 mmol), dimethylaminopyridine (0.01 g, 0.08 mmol) and N,N-diisopropylethylamine (0.3 mL, 1.7 mmol) in tetrahydrofuran (10 mL) at 0° C. was added benzoyl chloride (0.12 mL, 1.00 mmol). The resulting solution was warmed to ambient temperature and stirred for 18 hours, diluted with ethyl acetate (30 mL), washed with water (20 mL) and brine (20 mL). The organic solution was dried over anhydrous sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography to give 2-benzamido-N-benzylisonicotinamide (0.02 g, 15%): mp 174-176° C.; 1H NMR (300 MHz, CDCl3) δ 8.86 (br s, 1H), 8.72 (s, 1H), 8.38 (d, J=5.1 Hz, 1H), 7.91-7.82 (m, 2H), 7.60-7.32 (m, 9H), 6.73 (br s, 1H), 4.64 (d, J=5.7 Hz, 2H); 13C NMR (75 MHz, CDCl3) δ 165.9, 165.0, 151.9, 148.3, 144.4, 137.4, 133.5, 132.7, 129.0, 128.8, 128.0, 127.8, 127.2, 118.6, 110.5, 44.3; MS (ES+) m/z 332.5 (M+1).

후처리

  1. washwashed with water (20 mL) and brine (20 mL)
  2. dry with materialThe organic solution was dried over anhydrous sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography

출처 및 근거

ORD 기록
ord-89812048d6924ea0a37829aadf0445ab
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09187426B2

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