1-(2-Hydroxyethyl)piperazine → HCID 58368549, 화합물

HRID 1192598노트

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HRID 1192598 반응식
FC(F)(F)S(O[C:7]1[C:8]([C:18](=[O:20])[CH3:19])=[CH:9][C:10]([Cl:17])=[C:11]2[C:16]=1[N:15]=[CH:14][CH:13]=[CH:12]2)(=O)=O.[N:23]1([CH2:29][CH2:30][OH:31])[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1.C1C=CC(P(C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCCC1.ClCCl.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:17][C:10]1[CH:9]=[C:8]([C:18](=[O:20])[CH3:19])[C:7]([N:26]2[CH2:27][CH2:28][N:23]([CH2:29][CH2:30][OH:31])[CH2:24][CH2:25]2)=[C:16]2[C:11]=1[CH:12]=[CH:13][CH:14]=[N:15]2

참가 물질

8

반응물 4

HCID 76771-(2-Hydroxyethyl)piperazineHCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 58368658HCID 58368658, 화합물

생성물 1

HCID 58368549HCID 58368549, 화합물수율 14.1%

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매

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온도
65 °C

실험 절차

A stirred mixture of 7-acetyl-5-chloroquinolin-8-yl trifluoromethanesulfonate (0.12 g, 0.34 mmol, from Example 47, Step 2), 1-piperazineethanol (0.053 g, 0.41 mmol), palladium acetate (1.5 mg, 0.0068 mmol), (S)-(−)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (6.3 mg, 0.010 mmol), and cesium carbonate (0.31 g, 0.95 mmol) in tetrahydrofuran (3 mL) was heated at 65° C. overnight. The mixture was cooled, diluted with dichloromethane and filtered. The filtrate was washed with water, dried over MgSO4, evaporated to dryness. The resulting residue was purified on silica gel (eluting with 0 to 10% MeOH in dichloromethane) to give the desired product (16 mg, 14%). LCMS calculated for C17H21ClN3O2 (M+H)+: m/z=334.1; Found: 334.0.

후처리

  1. temperatureThe mixture was cooled
  2. filtrationfiltered
  3. washThe filtrate was washed with water
  4. dry with materialdried over MgSO4
  5. customevaporated to dryness
  6. customThe resulting residue was purified on silica gel (eluting with 0 to 10% MeOH in dichloromethane)

출처 및 근거

ORD 기록
ord-0c5b706578e946c3a2d6693d6e8b6022
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08680108B2

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