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 2056774노트

반응식

HRID 2056774 반응식
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]

참가 물질

8

반응물 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

생성물 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

시약·촉매·용매 3

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 1140Toluene용매HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-08be77cba73f4cf48204bfe2c56ec191
출처 데이터셋
uspto-grants-2008_02
특허 번호
US07335660B2

반응 노트

불러오는 중…