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Morpholine → HCID 66571344, 화합물

HRID 82008
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HRID 82008 반응식
[CH3:1][C:2]1[C:6]([C:7]2[C:8]([O:29][CH3:30])=[CH:9][C:10]3[C:11]4[N:19]([C@@H:20]([C:22]5[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=5)[CH3:21])[C:18](=O)[NH:17][C:12]=4[CH:13]=[N:14][C:15]=3[CH:16]=2)=[C:5]([CH3:31])[O:4][N:3]=1.O=P(Cl)(Cl)Cl.[NH:37]1[CH2:42][CH2:41][O:40][CH2:39][CH2:38]1>CN1C(=O)CCC1.CS(C)=O>[CH3:1][C:2]1[C:6]([C:7]2[C:8]([O:29][CH3:30])=[CH:9][C:10]3[C:11]4[N:19]([C@@H:20]([C:22]5[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=5)[CH3:21])[C:18]([N:37]5[CH2:42][CH2:41][O:40][CH2:39][CH2:38]5)=[N:17][C:12]=4[CH:13]=[N:14][C:15]=3[CH:16]=2)=[C:5]([CH3:31])[O:4][N:3]=1
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참가 물질

6

반응물 3

HCID 8083MorpholineHCID 24813Phosphorus oxychlorideHCID 529351837-(3,5-Dimethyl-4-isoxazolyl)-8-(methyloxy)-1-[(1R)-1-phenylethyl]-1,3-dihydro-2H-imidazo[4,5-c]quinolin-2-one

생성물 1

HCID 66571344HCID 66571344, 화합물수율 0.75%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매
HCID 13387
N-methyl-2-pyrrolidone
용매

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온도
100 °C

실험 절차

7-(3,5-Dimethyl-4-isoxazolyl)-8-(methyloxy)-1-[(1R)-1-phenylethyl]-1,3-dihydro-2H-imidazo[4,5-c]quinolin-2-one (for a preparation see Intermediate 11) (0.16 g, 0.386 mmol) was dissolved in POCl3 (1 ml, 10.73 mmol) and heated at 100° C. for 3 days. The reaction mixture was evaporated in vacuo to give a black gum. The residue was dissolved in NMP (2 ml) and morpholine (2 ml, 22.96 mmol) was added, then the solution was heated in the microwave at 150° C. for 1 h. The reaction mixture was loaded onto a 20 g SCX-2 cartridge and washed through with methanol (40 ml), then eluted with 2M methanolic ammonia and the eluant evaporated in vacuo to give an amber oil. This was dissolved in DMSO (1 ml) and purified by MDAP (HpH) to give 7-(3,5-dimethyl-4-isoxazolyl)-8-(methyloxy)-2-(4-morpholinyl)-1-[(1R)-1-phenylethyl]-1H-imidazo[4,5-c]quinoline (1.4 mg, 2.90 μmol, 0.750% yield). LCMS (formate) Rt 0.86 min, MH+ 484

후처리

  1. customThe reaction mixture was evaporated in vacuo
  2. customto give a black gum
  3. temperaturethe solution was heated in the microwave at 150° C. for 1 h
  4. washwashed through with methanol (40 ml)
  5. washeluted with 2M methanolic ammonia
  6. customthe eluant evaporated in vacuo
  7. customto give an amber oil
  8. custompurified by MDAP (HpH)

출처 및 근거

ORD 기록
ord-f52e2b1e01ab4a919fbdee63e3d1f7ab
출처 데이터셋
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08846709B2

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