Triethylamine → HCID 24949732, compound

HRID 1784363Notes

Reaction equation

HRID 1784363 reaction equation
C(N(CC)CC)C.[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.[C:23]1([C:29]([N:35]2[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]2)=[C:30]([C:33]#[N:34])[C:31]#[N:32])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=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:38]1[CH2:37][CH2:36][N:35]([C:29]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[C:30]([C:33]#[N:34])[C:31]#[N:32])[CH2:40][CH2:39]1)=[O:20])=[CH:12][NH:13]2

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 22888202HCID 22888202, compoundHCID 86616769HCID 86616769, compound

Product 1

HCID 24949732HCID 24949732, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Triethyl amine (2 ml) was added into a solution of 2-(4-fluoro-1H-indol-3-yl)-2-oxoacetyl chloride (284 mg) and 2-(phenyl(piperazin-1-yl)methylene)malononitrile (300 mg) in dry THF (20 ml). After 16 hours, the reaction mixture was partitioned between saturated NaHCO3 (20 ml) and EtOAc (20 ml), and the aqueous phase was extracted with EtOAc (3×20 ml). Then the combined organic layer was dried over MgSO4 and concentrated to offer a residue which was purified using Shimadzu automated preparative HPLC System to afford 2-((4-(2-(4-fluoro-1H-indol-3-yl)-2-oxoacetyl)piperazin-1-yl)(phenyl)methylene)malononitrile.

Workup

  1. customthe reaction mixture was partitioned between saturated NaHCO3 (20 ml) and EtOAc (20 ml)
  2. extractionthe aqueous phase was extracted with EtOAc (3×20 ml)
  3. dry with materialThen the combined organic layer was dried over MgSO4
  4. concentrationconcentrated
  5. customwas purified

Sources & evidence

ORD record
ord-38b7baa81a5a4dfba06ae10bb66987e8
Source dataset
uspto-grants-2009_03
Patent number
US07504399B2

Reaction notes

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