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Morpholine → HCID 66571344、化合物

HRID 82008
ノート
印刷プレビュー

反応式

HRID 82008 の反応式
[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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 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

生成物 1

HCID 66571344HCID 66571344、化合物収率 0.75%

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒
HCID 13387
N-methyl-2-pyrrolidone
溶媒

反応条件

温度
100 °C

実験手順

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

後処理

  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)

出典と根拠

ORDレコード
ord-f52e2b1e01ab4a919fbdee63e3d1f7ab
出典データセット
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08846709B2

反応ノート

読み込み中…

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