Triethylamine → HCID 45111502, compound

HRID 884761Notes

Reaction equation

HRID 884761 reaction equation
C(N(CC)CC)C.[C:8]([N:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1)([CH3:11])([CH3:10])[CH3:9].[CH:18]1([C@H:21]([NH:29][C:30]([C:32]2[C:41]3[C:36](=[C:37]([Cl:42])[CH:38]=[CH:39][CH:40]=3)[C:35](=[O:43])[N:34]([CH2:44][CH2:45][CH3:46])[C:33]=2[CH2:47]Br)=[O:31])[C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[CH:23]=2)[CH2:20][CH2:19]1.[OH-].[Na+]>C1COCC1>[CH:18]1([C@H:21]([NH:29][C:30]([C:32]2[C:41]3[C:36](=[C:37]([Cl:42])[CH:38]=[CH:39][CH:40]=3)[C:35](=[O:43])[N:34]([CH2:44][CH2:45][CH3:46])[C:33]=2[CH2:47][N:15]2[CH2:16][CH2:17][N:12]([C:8]([CH3:11])([CH3:10])[CH3:9])[CH2:13][CH2:14]2)=[O:31])[C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[CH:23]=2)[CH2:20][CH2:19]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 35305721-Tert-butylpiperazineHCID 86640260HCID 86640260, compound

Product 1

HCID 45111502HCID 45111502, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Triethyl amine (280 μL, 2 mmol) and 1-tert-butyl-piperazine (96 mg, 0.67 mmol) were added to 3-bromomethyl-8-chloro-1-oxo-2-propyl-1,2-dihydro-isoquinoline-4-carboxylic acid [(S)-cyclopropyl-(3-fluoro-phenyl)-methyl]-amide (0.56 mmol) in 10 mL THF. The reaction mixture was stirred at room temperature for 30 minutes and poured into 50 mL 0.5 N NaOH (aq). The mixture was extracted with ethyl acetate (100 mL). The organic phase was washed with brine, dried over MgSO4 and concentrated in vacuo. The crude product was flash chromatographed on silica gel (gradient heptane-ethyl acetate/methanol) to give 190 mg of the title compound, yield 60%. LC-MS (m/z) 567.8 (MH+); tR=1.07.

Workup

  1. extractionThe mixture was extracted with ethyl acetate (100 mL)
  2. washThe organic phase was washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customchromatographed on silica gel (gradient heptane-ethyl acetate/methanol)

Sources & evidence

ORD record
ord-1dd70b413a5140b2a8ac866bb0357cfd
Source dataset
uspto-grants-2012_08
Patent number
US08242134B2

Reaction notes

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