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

HRID 1807633ノート

反応式

HRID 1807633 の反応式
[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

参加物

6

反応物 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

生成物 1

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

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-2c2354355fb646f085656da99cee0b0c
出典データセット
uspto-grants-2013_01
特許番号
US08357687B2

反応ノート

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