Cyclohexylamine → HCID 59699642, 화합물

HRID 901241노트

반응식

HRID 901241 반응식
[CH:1]1([NH2:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C([O:10][C:11]([C:13]1[C:14](=[O:33])[N:15]([CH2:24][C:25]2[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=2)[C:16]2[C:21]([C:22]=1[OH:23])=[CH:20][CH:19]=[CH:18][N:17]=2)=O)C>C1(C)C(C)=CC=CC=1>[CH:1]1([NH:7][C:11]([C:13]2[C:14](=[O:33])[N:15]([CH2:24][C:25]3[CH:26]=[CH:27][C:28]([O:31][CH3:32])=[CH:29][CH:30]=3)[C:16]3[C:21]([C:22]=2[OH:23])=[CH:20][CH:19]=[CH:18][N:17]=3)=[O:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

참가 물질

4

반응물 2

HCID 7965CyclohexylamineHCID 59699551HCID 59699551, 화합물

생성물 1

HCID 59699642HCID 59699642, 화합물수율 82%

시약·촉매·용매 1

HCID 7237O-Xylene용매

반응 조건

온도
140 °C

실험 절차

Cyclohexylamine (1.18 mL, 10.35 mmol) was added to a stirred solution of 4-hydroxy-1-(4-methoxy-benzyl)-2-oxo-1,2-dihydro-[1,8]-naphthyridine-3-carboxylic acid ethyl ester (13) (1.80 g, 5.17 mmol) in xylene and heated at 140 ° C. for 3 h. The solution was cooled and the solvent was evaporated under vacuum. The residue was suspended in water and extracted by dichloromethane. The combined organic phase washed by water and brine, then dried over Na2SO4 and evaporated to yield 1.68 g (82%) of 4-hydroxy-1-(4-methoxy-benzyl)-2-oxo-1,2-dihydro-[1,8]-naphthyridine-3-carboxylic acid cyclohexylamide (29) as white solids. MP: 149° C.; 1H-NMR (DMSO-d6): δ 1.2-1.4 (m, 5H), 1.55 (m, 1H), 1.70 (m, 2H), 1.90 (m, 2H), 3.69 (s, 3H), 3.86 (m, 1H), 5.54 (s, 2H), 6.81 (d, J=8.8 Hz, 2H), 7.20 (d, J=8.8 Hz, 2H), 7.43 (m, 1H), 8.47 (dd, J=2.0, 8.0 Hz, 1H), 8.79 (dd, J=1.6, 4.8 Hz, 1H), 10.22 (d, J=7.2 Hz, 1H); EIMS m/z 408 (M+1).

후처리

  1. temperatureThe solution was cooled
  2. customthe solvent was evaporated under vacuum
  3. extractionextracted by dichloromethane
  4. washThe combined organic phase washed by water and brine
  5. dry with materialdried over Na2SO4
  6. customevaporated

출처 및 근거

ORD 기록
ord-4842fd0cb2ee4e5bbe80c81fbc809c9c
출처 데이터셋
uspto-grants-2008_04
특허 번호
US07361760B2

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