2-Imidazolidinone → 1-((1S)-1-{2-[(2R)-4-(6-Cyano-1-benzothien-3-yl)-2-methylpiperazinyl]ethyl}-3,4-dihydro-1H-2-benzopyran-6-yl)-2-imidazolidinone

HRID 2056774Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2056774
Br[C:2]1[CH:3]=[CH:4][C:5]2[C@H:10]([CH2:11][CH2:12][N:13]3[CH2:18][CH2:17][N:16]([C:19]4[C:23]5[CH:24]=[CH:25][C:26]([C:28]#[N:29])=[CH:27][C:22]=5[S:21][CH:20]=4)[CH2:15][C@H:14]3[CH3:30])[O:9][CH2:8][CH2:7][C:6]=2[CH:31]=1.[NH:32]1[CH2:36][CH2:35][NH:34][C:33]1=[O:37].C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>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:28]([C:26]1[CH:25]=[CH:24][C:23]2[C:19]([N:16]3[CH2:17][CH2:18][N:13]([CH2:12][CH2:11][C@H:10]4[C:5]5[CH:4]=[CH:3][C:2]([N:32]6[CH2:36][CH2:35][NH:34][C:33]6=[O:37])=[CH:31][C:6]=5[CH2:7][CH2:8][O:9]4)[C@H:14]([CH3:30])[CH2:15]3)=[CH:20][S:21][C:22]=2[CH:27]=1)#[N:29]

Komponenten

8

Edukt 4

HCID 84532-ImidazolidinoneHCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 693073673-((3R)-4-{2-[(1S)-6-Bromo-3,4-dihydro-1H-2-benzopyran-1-yl]ethyl}-3-methylpiperazinyl)-1-benzothiophene-6-carbonitrile

Produkt 1

HCID 693078161-((1S)-1-{2-[(2R)-4-(6-Cyano-1-benzothien-3-yl)-2-methylpiperazinyl]ethyl}-3,4-dihydro-1H-2-benzopyran-6-yl)-2-imidazolidinone

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 1140TolueneLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

3-((3R)-4-{2-[(1S)-6-Bromo-3,4-dihydro-1H-2-benzopyran-1-yl]ethyl}-3-methylpiperazinyl)-1-benzothiophene-6-carbonitrile (0.36 g, 0.73 mmol)was dissolved in dry toluene (15 mL) and degassed. 2-Imidazolidinone (0.071 g, 0.82 mmol), tris(dibenzylideneacetone)dipalladium (34 mg), (+/−)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (47 mg) and caesium carbonate (0.34 g, 1.05 mmol)were added and the mixture heated under reflux with stirring, under a nitrogen atmosphere, for 2 days. The reaction was cooled to room temperature, diluted with dichloromethane, filtered through celite and washed with water. The organic extracts were dried (MgSO4), filtered and evaporated in vacuo. Purification by LC-MS yielded the title compound as the free base. M+H=502.

Aufarbeitung

  1. customdegassed
  2. temperaturethe mixture heated
  3. temperatureunder reflux
  4. filtrationfiltered through celite
  5. washwashed with water
  6. dry with materialThe organic extracts were dried (MgSO4)
  7. filtrationfiltered
  8. customevaporated in vacuo
  9. customPurification by LC-MS

Quellen und Nachweise

ORD-Eintrag
ord-08be77cba73f4cf48204bfe2c56ec191
Quelldatensatz
uspto-grants-2008_02
Patentnummer
US07335660B2

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