1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 1'-[(1-Cyclopropyl-4-methoxy-1H-indol-6-yl)carbonyl]-6-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)spiro[chroman-2,4'-piperidin]-4-one

HRID 420121노트

반응식

HRID 420121 반응식
C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.[CH:22]1([N:25]2[C:33]3[C:28](=[C:29]([O:37][CH3:38])[CH:30]=[C:31]([C:34]([OH:36])=O)[CH:32]=3)[CH:27]=[CH:26]2)[CH2:24][CH2:23]1.Cl.[O:40]=[C:41]1[O:45][N:44]=[C:43]([C:46]2[CH:47]=[C:48]3[C:58](=[CH:59][CH:60]=2)[O:57][C:51]2([CH2:56][CH2:55][NH:54][CH2:53][CH2:52]2)[CH2:50][C:49]3=[O:61])[NH:42]1>CN(C=O)C.O.CCN(CC)CC>[CH:22]1([N:25]2[C:33]3[C:28](=[C:29]([O:37][CH3:38])[CH:30]=[C:31]([C:34]([N:54]4[CH2:55][CH2:56][C:51]5([CH2:50][C:49](=[O:61])[C:48]6[C:58](=[CH:59][CH:60]=[C:46]([C:43]7[NH:42][C:41](=[O:40])[O:45][N:44]=7)[CH:47]=6)[O:57]5)[CH2:52][CH2:53]4)=[O:36])[CH:32]=3)[CH:27]=[CH:26]2)[CH2:23][CH2:24]1

참가 물질

8

반응물 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 666494031-cyclopropyl-4-methoxy-1H-indole-6-carboxylic acidHCID 1363426496-(5-Oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)spiro[chroman-2,4'-piperidin]-4-one hydrochloride

생성물 1

HCID 1362001361'-[(1-Cyclopropyl-4-methoxy-1H-indol-6-yl)carbonyl]-6-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)spiro[chroman-2,4'-piperidin]-4-one

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8471Triethylamine용매

실험 절차

Et3N (58 μL), HOBT (32 mg) and WSC (40 mg) were added to a solution of 1-cyclopropyl-4-methoxy-1H-indol-6-carboxylic acid (40 mg) and 6-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)spiro[chroman-2,4′-piperidin]-4-one hydrochloride (70 mg) in DMF (4 mL), and stirred overnight at room temperature. Water was added to the reaction mixture, and the formed solid was collected by filtration. The solid was washed thoroughly with water and ether. This was dried under reduced pressure to obtain the title compound. 1H-NMR (400 MHz, DMSO-d6) δ: 12.91 (1H, brs), 8.20 (1H, d, J=4.0 Hz), 8.00 (1H, dd, J=8.0, 4.0 Hz), 7.36-7.26 (2H, m), 7.22 (1H, s), 6.57 (1H, s), 6.39 (1H, d, J=4.0 Hz), 4.20-4.00 (1H, m), 3.87 (3H, s), 3.46-3.40 (1H, m), 3.40-3.20 (3H, m), 2.89 (2H, s), 2.06-1.77 (4H, m), 1.07-1.03 (2H, m), 0.94-0.90 (2H, m); MS [M+H]+=515.

후처리

  1. filtrationthe formed solid was collected by filtration
  2. washThe solid was washed thoroughly with water and ether
  3. customThis was dried under reduced pressure

출처 및 근거

ORD 기록
ord-8d7bde5ba6754f45a43746796724a007
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08093389B2

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