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Morpholine → Isopropyl 5-[acetyl-(3,5-bistrifluoromethylbenzyl)amino]-8-morpholin-4-yl-2,3,4,5-tetrahydrobenzo[b]azepine-1-carboxylate

HRID 2353882
ノート
印刷プレビュー

反応式

HRID 2353882 の反応式
CC(C)([O-])C.[Na+].[NH:7]1[CH2:12][CH2:11][O:10][CH2:9][CH2:8]1.[CH:13]([O:16][C:17]([N:19]1[CH2:25][CH2:24][CH2:23][CH:22]([N:26]([C:42](=[O:44])[CH3:43])[CH2:27][C:28]2[CH:33]=[C:32]([C:34]([F:37])([F:36])[F:35])[CH:31]=[C:30]([C:38]([F:41])([F:40])[F:39])[CH:29]=2)[C:21]2[CH:45]=[CH:46][C:47](Br)=[CH:48][C:20]1=2)=[O:18])([CH3:15])[CH3:14]>C1(C)C=CC=CC=1.ClCCl.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:42]([N:26]([CH2:27][C:28]1[CH:33]=[C:32]([C:34]([F:37])([F:36])[F:35])[CH:31]=[C:30]([C:38]([F:40])([F:39])[F:41])[CH:29]=1)[CH:22]1[CH2:23][CH2:24][CH2:25][N:19]([C:17]([O:16][CH:13]([CH3:15])[CH3:14])=[O:18])[C:20]2[CH:48]=[C:47]([N:7]3[CH2:12][CH2:11][O:10][CH2:9][CH2:8]3)[CH:46]=[CH:45][C:21]1=2)(=[O:44])[CH3:43]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 3

HCID 8083MorpholineHCID 23676156Sodium t-butoxideHCID 59003154Isopropyl 5-[acetyl-(3,5-bistrifluoromethylbenzyl)amino]-8-bromo-2,3,4,5-tetrahydrobenzo[b]azepine-1-carboxylate

生成物 1

HCID 59003217Isopropyl 5-[acetyl-(3,5-bistrifluoromethylbenzyl)amino]-8-morpholin-4-yl-2,3,4,5-tetrahydrobenzo[b]azepine-1-carboxylate

試薬・触媒・溶媒 3

HCID 9811564
Bis(dibenzylideneacetone)palladium
触媒
HCID 1140Toluene溶媒
HCID 6344Dichloromethane溶媒

実験手順

Combine tris(dibenzylideneacetone)dipalladium (0) (0.015 g, 0.017 mmol), 2,2′-bis(diphenylphosphino)-1,1′-binaphyl (0.031 g, 0.050 mmol) and sodium t-butoxide (0.023 g, 0.235 mmol) in toluene (3 mL) in a 10 mL microwave vessel and purge this suspension with nitrogen at room temperature for 5 min. Add morpholine (0.016 mL, 0.185 mmol) followed by isopropyl-5-[acetyl-(3,5-bistrifluoromethylbenzyl)amino]-8-bromo-2,3,4,5-tetrahydrobenzo[b]azepine-1-carboxylate (0.100 g, 0.168 mmol) and irradiate this mixture at 110° C. for 15 min. Dilute the cooled mixture with dichloromethane and filter through Celite. Remove the filtrate solvent under reduced pressure and purify the residue using chromatography on silica gel, eluting with hexanes/ethyl acetate (60:40), to provide the title compound a yellow solid (0.041 g, 40%): ESI MS 602 (M+H)

後処理

  1. customirradiate this mixture at 110° C. for 15 min
  2. filtrationfilter through Celite
  3. customRemove the filtrate solvent under reduced pressure
  4. custompurify the residue
  5. washeluting with hexanes/ethyl acetate (60:40)

出典と根拠

ORDレコード
ord-97d58a0d0b054e3ea749a806a412cf95
出典データセット
uspto-grants-2010_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07749992B2

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート