Triethylamine → HCID 16040305, compound

HRID 747095Notes

Reaction equation

HRID 747095 reaction equation
CCN(CC)CC.[F:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[C:11]([C:18](=[O:22])[C:19](Cl)=[O:20])=[CH:12][NH:13]2.OC(C(F)(F)F)=O.[C:30]1([C:36]([N:38]2[CH2:43][CH2:42][NH:41][CH2:40][CH2:39]2)=[NH:37])[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>C1COCC1>[F:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[C:11]([C:18](=[O:22])[C:19]([N:41]1[CH2:42][CH2:43][N:38]([C:36](=[NH:37])[C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH2:39][CH2:40]1)=[O:20])=[CH:12][NH:13]2

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 22888202HCID 22888202, compoundHCID 86611691HCID 86611691, compound

Product 1

HCID 16040305HCID 16040305, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Et3N (2 ml) was added into a solution of 2-(4-fluoro-1H-indol-3-yl)-2-oxoacetyl chloride (1.56 g) and phenyl(piperazin-1-yl)methanimine TFA salt (1.98 g) in THF (20 ml) and reaction was stirred at room temperature for 17 hours before quenched with saturated aqueous NaHCO3 solution (50 ml). The aqueous layer was extracted with ethyl acetate (3×50 ml). The organic phase combined and dried over anhydrous MgSO4. Concentration in vacuo provided a crude product, which was purified by silica gel column chromatography to afford 1-(4-fluoro-1H-indol-3-yl)-2-(4-(imino(phenyl)methyl)piperazin-1-yl)ethane-1,2-dione.

Workup

  1. custombefore quenched with saturated aqueous NaHCO3 solution (50 ml)
  2. extractionThe aqueous layer was extracted with ethyl acetate (3×50 ml)
  3. dry with materialdried over anhydrous MgSO4
  4. concentrationConcentration in vacuo
  5. customprovided a crude product, which
  6. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-a383b497513444b7a3402a833308c8d2
Source dataset
uspto-grants-2008_07
Patent number
US07396830B2

Reaction notes

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