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 2056774ノート

反応式

HRID 2056774 の反応式
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]

参加物

8

反応物 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

生成物 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

試薬・触媒・溶媒 3

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

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-08be77cba73f4cf48204bfe2c56ec191
出典データセット
uspto-grants-2008_02
特許番号
US07335660B2

反応ノート

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