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Morpholine → 2-[2-({3-[4-(morpholine-4-carbonyl)phenoxy]propyl}-pyridin-4-ylmethylamino)ethyl]-2H-isoquinolin-1-one dihydrochloride

HRID 69013
ノート
印刷プレビュー

反応式

HRID 69013 の反応式
Br[C:2]1[CH:32]=[CH:31][C:5]([O:6][CH2:7][CH2:8][CH2:9][N:10]([CH2:24][C:25]2[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=2)[CH2:11][CH2:12][N:13]2[CH:22]=[CH:21][C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14]2=[O:23])=[CH:4][CH:3]=1.[C:33](=[O:36])([O-])[O-].[Na+].[Na+].[NH:39]1[CH2:44][CH2:43][O:42][CH2:41][CH2:40]1.C(OC(=O)C)C.[ClH:51]>C(=[Mo](=C=O)(=C=O)(=C=O)(=C=O)=C=O)=O.CC1C(P(C2C([CH2-])=CC=CC=2)C2C(C)=CC=CC=2)=CC=CC=1.CC1C(P(C2C([CH2-])=CC=CC=2)C2C(C)=CC=CC=2)=CC=CC=1.CC(O)=O.CC(O)=O.[Pd].[Pd].C(OCC)(=O)C.O.C1COCC1>[ClH:51].[ClH:51].[N:39]1([C:33]([C:2]2[CH:3]=[CH:4][C:5]([O:6][CH2:7][CH2:8][CH2:9][N:10]([CH2:24][C:25]3[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=3)[CH2:11][CH2:12][N:13]3[CH:22]=[CH:21][C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[C:14]3=[O:23])=[CH:31][CH:32]=2)=[O:36])[CH2:44][CH2:43][O:42][CH2:41][CH2:40]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

10

反応物 4

HCID 8083MorpholineHCID 10340Sodium CarbonateHCID 21866389Hydrogen chloride-ethyl acetateHCID 669599672-(2-{[3-(4-Bromophenoxy)propyl]pyridin-4-ylmethylamino}ethyl)-2H-isoquinolin-1-one

生成物 1

HCID 669600602-[2-({3-[4-(morpholine-4-carbonyl)phenoxy]propyl}-pyridin-4-ylmethylamino)ethyl]-2H-isoquinolin-1-one dihydrochloride

試薬・触媒・溶媒 5

HCID 11104995trans-Bis(acetato)bis[2-[bis(2-methylphenyl)phosphino]benzyl]dipalladium(II)触媒HCID 178521658HCID 178521658、化合物触媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒2 回

反応条件

温度
170 °C

実験手順

2-(2-{[3-(4-Bromophenoxy)propyl]pyridin-4-ylmethylamino}ethyl)-2H-isoquinolin-1-one (500 mg), hexacarbonyl molybdenum (264 mg), trans-di-μ-acetatobis[2-(di-o-tolylphosphino)benzyl]dipalladium (II) (Herrmann's palladacycle)(23 mg), sodium carbonate (318 mg), and morpholine (0.26 ml) were added to THF (5 ml). The mixture was heated at 170° C. for 10 minutes (microwave reactor). The reaction mixture was cooled to room temperature. Water and ethyl acetate were added thereto, followed by celite filtration. The organic layer was dried with sodium sulfate, and condensed under reduced pressure. The residue was purified by NH silica gel column chromatography (ethyl acetate:methanol=1:0→7:3). The purified product was condensed under reduced pressure. A 4N-hydrogen chloride ethyl acetate solution was added to an ethyl acetate solution of the residue. The precipitated insoluble matter was separated, washed with ethyl acetate, and dried to give the title compound (150 mg) as a white powder.

後処理

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationfollowed by celite filtration
  3. dry with materialThe organic layer was dried with sodium sulfate, and condensed under reduced pressure
  4. customThe residue was purified by NH silica gel column chromatography (ethyl acetate:methanol=1:0→7:3)
  5. customcondensed under reduced pressure
  6. customThe precipitated insoluble matter was separated
  7. washwashed with ethyl acetate
  8. customdried

出典と根拠

ORDレコード
ord-45d6a4a53cf54b04bafcdf03335ae721
出典データセット
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08822453B2

反応ノート

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