Triethylamine → HCID 23614975, compound

HRID 1768316Notes

Reaction equation

HRID 1768316 reaction equation
C[O:2][C:3](=[O:25])[C:4]1[CH:9]=[C:8]([N:10]2[C:15](=[O:16])[N:14]([CH2:17][CH:18]([OH:22])[CH2:19][O:20][CH3:21])[C:13](=[O:23])[CH:12]=[N:11]2)[CH:7]=[CH:6][C:5]=1[Cl:24].C(N(CC)CC)C.[Si:33](Cl)([C:36]([CH3:39])([CH3:38])[CH3:37])([CH3:35])[CH3:34].[OH-].[Na+]>C1COCC1>[C:36]([Si:33]([CH3:35])([CH3:34])[O:22][CH:18]([CH2:19][O:20][CH3:21])[CH2:17][N:14]1[C:13](=[O:23])[CH:12]=[N:11][N:10]([C:8]2[CH:7]=[CH:6][C:5]([Cl:24])=[C:4]([CH:9]=2)[C:3]([OH:2])=[O:25])[C:15]1=[O:16])([CH3:39])([CH3:38])[CH3:37]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 28928tert-Butyldimethylsilyl chlorideHCID 69344114HCID 69344114, compound

Product 1

HCID 23614975HCID 23614975, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To Intermediate 2 (14.8 g, 40 mmol) in THF (200 ml) and triethylamine (44 mmol, 4.45) at 0° C., is added t-butyldimethylsilylchloride (TBDMS-Cl) (44 mmol, 6.63 g). The reaction is allowed to warm to room temperature and stirred overnight. 1 N NaOH solution (100 ml) is added, and the reaction is stirred at 40° C. for 4 h. THF is evaporated under reduced pressure, and the resulting mixture is acidified with 1 N HCl to pH<2. The mixture is extracted with ethyl acetate (2×100 ml). The organic phase is washed with brine solution, dried over MgSO4, and concentrated in vacuo to give 5-{4-[2-(tert-Butyl-dimethyl-silanyloxy)-3-methoxy-propyl]-3,5-dioxo-4,5-dihydro-3H-[1,2,4]triazin-2-yl}-2-chloro-benzoic acid.

Workup

  1. stirringthe reaction is stirred at 40° C. for 4 h
  2. customTHF is evaporated under reduced pressure
  3. extractionThe mixture is extracted with ethyl acetate (2×100 ml)
  4. washThe organic phase is washed with brine solution
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b97611f3ffe044a6b839671c6741506a
Source dataset
uspto-grants-2007_06
Patent number
US07235657B2

Reaction notes

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