Acetic Acid → HCID 178522006, 화합물

HRID 1376212노트

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HRID 1376212 반응식
C(OC(NC1CCCC(C(O)=O)C1)=O)C1C=CC=CC=1.C1C=CC2N(O)N=NC=2C=1.NC1C(=O)N(CC2C=CC=CC=2)C=CC=1N.CCN=C=NCCCN(C)C.[CH2:58]([O:65][C:66](=[O:92])[NH:67][CH:68]1[CH2:73][CH2:72][CH2:71][CH:70]([C:74](=O)[NH:75][C:76]2[C:77](=[O:90])[N:78]([CH2:83][C:84]3[CH:89]=[CH:88][CH:87]=[CH:86][CH:85]=3)[CH:79]=[CH:80][C:81]=2[NH2:82])[CH2:69]1)[C:59]1[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=1.C(O)(=O)C>CN(C=O)C.O>[CH2:58]([O:65][C:66](=[O:92])[NH:67][CH:68]1[CH2:73][CH2:72][CH2:71][CH:70]([C:74]2[NH:75][C:76]3[C:77](=[O:90])[N:78]([CH2:83][C:84]4[CH:89]=[CH:88][CH:87]=[CH:86][CH:85]=4)[CH:79]=[CH:80][C:81]=3[N:82]=2)[CH2:69]1)[C:59]1[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=1

참가 물질

9

반응물 6

HCID 176Acetic AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 219476293,4-diamino-1-benzyl-1H-pyridin-2-oneHCID 446300243-{[(Benzyloxy)carbonyl]amino}cyclohexane-1-carboxylic acidHCID 68546350[3-(4-Amino-1-benzyl-2-oxo-1,2-dihydro-pyridin-3-ylcarbamoyl)-cyclohexyl]-carbamic acid benzyl ester

생성물 1

HCID 178522006HCID 178522006, 화합물수율 45.6%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

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온도
0 °C

실험 절차

3-Benzyloxycarbonylamino-cyclohexanecarboxylic acid (0.52 g, 1.86 mmol), TEA (0.41 g, 4.09 mmol), and HOBt (0.50 g, 3.72 mmol) were added sequentially to a solution of 3,4-diamino-1-benzyl-1H-pyridin-2-one (0.40 g, 1.86 mmol) in DMF (15 mL) at room temp. After the solution was cooled to 0° C., EDCI (0.71 g, 3.72 mmol) was added and the resulting solution was allowed to stir, with warming to room temp, for 17 h. The reaction mixture was diluted with water (10 mL) extracted with CH2Cl2, dried with MgSO4, and concentrated. The crude [3-(4-amino-1-benzyl-2-oxo-1,2-dihydro-pyridin-3-ylcarbamoyl)-cyclohexyl]-carbamic acid benzyl ester (0.57 g, 1.20 mmol) was dissolved in glacial acetic acid (7.21 g, 120.1 mmol), and heated at 120° C. for 2 days. After cooling to room temperature, the solvent was evaporated under reduced pressure and the cyclized product was purified by flash chromatography, eluting with 3% MeOH in CH2Cl2 to give [3-(5-benzyl-4-oxo-4,5-dihydro-3H-imidazo[4,5-c]pyridin-2-yl)-cyclohexyl]-carbamic acid benzyl ester (0.25 g, 30% for 2 steps). 1H-NMR (DMSO): δ 7.46 (m, 1H), 7.25–7.38 (m, 10H), 6.57 (m, 1H), 5.20 (s, 2H), 5.01 (s, 2H), 3.41 (m, 1H), 2.89 (m, 1H), 2.13 (m, 1H), 1.80 (m, 3H), 1.42 (m, 2H), 1.21 (m, 2H). MS: calculated for C27H28N4O3+H 457.2; found: 457.5.

후처리

  1. temperaturewith warming to room temp, for 17 h
  2. extractionextracted with CH2Cl2
  3. dry with materialdried with MgSO4
  4. concentrationconcentrated
  5. temperatureheated at 120° C. for 2 days
  6. temperatureAfter cooling to room temperature
  7. customthe solvent was evaporated under reduced pressure
  8. customthe cyclized product was purified by flash chromatography
  9. washeluting with 3% MeOH in CH2Cl2

출처 및 근거

ORD 기록
ord-3e17d94edc6340edb23e5eb0a6603a5f
출처 데이터셋
uspto-grants-2007_01
특허 번호
US07169926B1

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