Triethylamine → SB 414240

HRID 1166275노트

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HRID 1166275 반응식
Cl.Cl.[N:3]1([CH:9]2[CH2:14][CH2:13][N:12]([CH2:15][C:16]3[C:17]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)=[N:18][C:19]4[C:24]([C:25]=3[C:26](O)=[O:27])=[CH:23][CH:22]=[CH:21][CH:20]=4)[CH2:11][CH2:10]2)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.[CH3:35][C@H:36]([NH2:41])[C:37]([CH3:40])([CH3:39])[CH3:38].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C>C1COCC1.C(Cl)Cl>[CH3:35][C@H:36]([NH:41][C:26]([C:25]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[N:18]=[C:17]([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[C:16]=1[CH2:15][N:12]1[CH2:11][CH2:10][CH:9]([N:3]2[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]2)[CH2:14][CH2:13]1)=[O:27])[C:37]([CH3:40])([CH3:39])[CH3:38]

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 7004913(2S)-3,3-dimethylbutan-2-amineHCID 695475013-[1,4']Bipiperidinyl-1'-ylmethyl-2-phenyl-quinoline-4-carboxylic acid dihydrochloride

생성물 1

HCID 9806459SB 414240수율 60.2%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매

실험 절차

539 mg (0.94 mmol) of 3-[1,4′]bipiperidinyl-1′-ylmethyl-2-phenyl-quinoline-4-carboxylic acid dihydrochloride (compound of Description 6), 202 microliters (1.5 mmol) of (S)-1,2,2-trimethyl-propylamine (Lancaster), 570 mg (1.5 mmol) of HBTU, 610 microliters (4.4 mmol) of triethylamine were dissolved in 12 ml THF and 8.5 ml of CH2Cl2 and the mixture was refluxed for 18 h. The solvent was concentrated, the residue was dissolved in methylene chloride, washed with water, then with 0.5 N aqueous NaOH, again with water, and the organic phase was dried over MgSO4. After concentration of the solvent, the residue was purified by flash chromatography over 40 g of silicagel (eluent EtOAc/MeOH/NH4OH:90/10/0.1), affording 290 mg (yield 56%) of the title compound as a beige amorphous solid.

후처리

  1. concentrationThe solvent was concentrated
  2. dissolutionthe residue was dissolved in methylene chloride
  3. washwashed with water
  4. dry with materialwith 0.5 N aqueous NaOH, again with water, and the organic phase was dried over MgSO4
  5. customAfter concentration of the solvent, the residue was purified by flash chromatography over 40 g of silicagel (eluent EtOAc/MeOH/NH4OH:90/10/0.1)

출처 및 근거

ORD 기록
ord-a571bead09c24e15aa567a9fcfc4ad8f
출처 데이터셋
uspto-grants-2003_09
특허 번호
US06613770B1

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