Diisopropylethylamine → 1-(4,4-difluorocyclohexyl)-7-[(5-fluoro-2,3-dihydro-1H-indol-1-yl)carbonyl]-8-methyl[1,2,4]triazolo[4,3-a]quinoxalin-4(5H)-one

HRID 1807876노트

반응식

HRID 1807876 반응식
[F:1][C:2]1([F:26])[CH2:7][CH2:6][CH:5]([C:8]2[N:12]3[C:13]4[C:18]([NH:19][C:20](=[O:21])[C:11]3=[N:10][N:9]=2)=[CH:17][C:16]([C:22](O)=[O:23])=[C:15]([CH3:25])[CH:14]=4)[CH2:4][CH2:3]1.[F:27][C:28]1[CH:29]=[C:30]2[C:34](=[CH:35][CH:36]=1)[NH:33][CH2:32][CH2:31]2.C(N(C(C)C)CC)(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>O.CN(C)C=O>[F:26][C:2]1([F:1])[CH2:3][CH2:4][CH:5]([C:8]2[N:12]3[C:13]4[C:18]([NH:19][C:20](=[O:21])[C:11]3=[N:10][N:9]=2)=[CH:17][C:16]([C:22]([N:33]2[C:34]3[C:30](=[CH:29][C:28]([F:27])=[CH:36][CH:35]=3)[CH2:31][CH2:32]2)=[O:23])=[C:15]([CH3:25])[CH:14]=4)[CH2:6][CH2:7]1

참가 물질

7

반응물 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 27744635-FluoroindolineHCID 58575300HCID 58575300, 화합물

생성물 1

HCID 469101431-(4,4-difluorocyclohexyl)-7-[(5-fluoro-2,3-dihydro-1H-indol-1-yl)carbonyl]-8-methyl[1,2,4]triazolo[4,3-a]quinoxalin-4(5H)-one수율 54.2%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

To a mixture of 150 mg of 1-(4,4-difluorocyclohexyl)-8-methyl-4-oxo-4,5-dihydro[1,2,4]triazolo[4,3-a]quinoxaline-7-carboxylic acid, 62.5 mg of 5-fluoroindoline, 0.25 mL of diisopropylethylamine, and 3 mL of N,N-dimethylformamide was added 146 mg of TBTU, followed by stirring at room temperature overnight. To the reaction liquid were added water and a saturated aqueous sodium hydrogen carbonate solution, followed by extraction with chloroform. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, and then the solvent was evaporated. The obtained residue was purified by silica gel column chromatography (chloroform/methanol=100/0 to 95/5). The obtained solid was washed with a mixed solution of hot diethyl ether and normal hexane to obtain 108 mg of 1-(4,4-difluorocyclohexyl)-7-[(5-fluoro-2,3-dihydro-1H-indol-1-yl)carbonyl]-8-methyl[1,2,4]triazolo[4,3-a]quinoxalin-4(5H)-one.

후처리

  1. customTo the reaction liquid
  2. extractiona saturated aqueous sodium hydrogen carbonate solution, followed by extraction with chloroform
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated
  6. customThe obtained residue was purified by silica gel column chromatography (chloroform/methanol=100/0 to 95/5)
  7. washThe obtained solid was washed with a mixed solution of hot diethyl ether and normal hexane

출처 및 근거

ORD 기록
ord-b9a78c5ef9bb41328d786e2de55cca10
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08357688B2

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