Triethylamine → SB 414240

HRID 1166275Notes

Reaction equation

HRID 1166275 reaction equation
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]

Participants

7

Reactant 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

Product 1

HCID 9806459SB 414240Yield 60.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-a571bead09c24e15aa567a9fcfc4ad8f
Source dataset
uspto-grants-2003_09
Patent number
US06613770B1

Reaction notes

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