Tetrahydrofuran → methyl 3-cyclohexyl-1-methyl-2-{2-[2-(methyl {2-[2-(methylamino)ethoxy]ethyl}amino)-2-oxoethoxy]phenyl}-1H-indole-6-carboxylate

HRID 1807633노트

반응식

HRID 1807633 반응식
[CH:1]1([C:7]2[C:15]3[C:10](=[CH:11][C:12]([C:16]([O:18][CH3:19])=[O:17])=[CH:13][CH:14]=3)[N:9]([CH3:20])[C:8]=2[C:21]2[CH:31]=[CH:30][CH:29]=CC=2OCC(O)=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:32][NH:33][CH2:34][CH2:35][O:36][CH2:37][CH2:38][NH:39][CH3:40].C(N(C(C)C)CC)(C)C.CN(C([O:57]N1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH2:74]1[CH2:78][O:77][CH2:76][CH2:75]1>>[CH:1]1([C:7]2[C:15]3[C:10](=[CH:11][C:12]([C:16]([O:18][CH3:19])=[O:17])=[CH:13][CH:14]=3)[N:9]([CH3:20])[C:8]=2[C:21]2[CH:31]=[CH:30][CH:29]=[CH:75][C:76]=2[O:77][CH2:78][C:74]([N:33]([CH3:32])[CH2:34][CH2:35][O:36][CH2:37][CH2:38][NH:39][CH3:40])=[O:57])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

참가 물질

6

반응물 5

HCID 8028TetrahydrofuranHCID 81531DiisopropylethylamineHCID 27247701,5-Bis(methylamino)-3-oxapentaneHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 58317804{2-[3-cyclohexyl-6-(methoxycarbonyl)-1-methyl-1H-indol-2-yl]phenoxy}acetic acid

생성물 1

HCID 67226641methyl 3-cyclohexyl-1-methyl-2-{2-[2-(methyl {2-[2-(methylamino)ethoxy]ethyl}amino)-2-oxoethoxy]phenyl}-1H-indole-6-carboxylate수율 91%

실험 절차

A solution of intermediate 5 (650 mg, 1.54 mmol), N-methyl-2-(methylaminoethyloxy)ethylamine (1.02 g, 7.71 mmol), diisopropylethylamine (808 μL, 4.63 mmol) and HATU (880 mg, 2.31 mmol) in dry THF (25 mL) was stirred at room temperature overnight. Then, the reaction mixture was concentrated under vacuum. The residue was partitioned between AcOEt and water. The organic layer was dried over anhydrous Na2SO4 and evaporated to yield 750 mg (91%) of methyl 3-cyclohexyl-1-methyl-2-{2-[2-(methyl {2-[2-(methylamino)ethoxy]ethyl}amino)-2-oxoethoxy]phenyl}-1H-indole-6-carboxylate 6: m/z=536 (M+H)+.

후처리

  1. concentrationThen, the reaction mixture was concentrated under vacuum
  2. customThe residue was partitioned between AcOEt and water
  3. dry with materialThe organic layer was dried over anhydrous Na2SO4
  4. customevaporated

출처 및 근거

ORD 기록
ord-2c2354355fb646f085656da99cee0b0c
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08357687B2

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