Triethylamine → HCID 58981001, compound

HRID 1181794Notes

Reaction equation

HRID 1181794 reaction equation
[CH2:1]([N:5]1[C:10]([NH:11][N:12]=[CH:13][C:14]2[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=3[S:16][CH:15]=2)=[CH:9][C:8](=[O:23])[N:7]([CH3:24])[C:6]1=[O:25])[CH:2]([CH3:4])[CH3:3].[CH3:26][N:27]1[CH:31]=[CH:30][CH:29]=[C:28]1[CH:32]=O.C(N(CC)CC)C>CC(N(C)C)=O>[S:16]1[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[C:14]([CH2:13][N:12]2[C:32]([C:28]3[N:27]([CH3:26])[CH:31]=[CH:30][CH:29]=3)=[C:9]3[C:10]([N:5]([CH2:1][CH:2]([CH3:4])[CH3:3])[C:6](=[O:25])[N:7]([CH3:24])[C:8]3=[O:23])=[N:11]2)=[CH:15]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 145041-Methyl-1H-pyrrole-2-carbaldehydeHCID 69429449HCID 69429449, compound

Product 1

HCID 58981001HCID 58981001, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
90 °C

Procedure

1-Benzothiophene-3-carbaldehyde N-(3-isobutyl-1-methyl-2,6-dioxo-1,2,3,6-tetrahydro-4-pyrimidinyl)hydrazone (100 mg, 0.284 mmol) was suspended in anh. DMA (3 mL) under an atmosphere of N2 gas. To the suspension was added N-methylpyrrole-2-carboxaldehyde (37 mg, 0.34 mmol). To this suspension was added catalytic amounts of triethylamine (25 μL). The reaction mixture was placed in a preheated heating block maintained at 90° C. and heated under N2 gas for 18 h. At the end of reaction the solvent was removed in vacuo and the resulting brown oil was resuspended in DMSO (1.5 mL) and was purified by semi preparative RPHPLC eluting with MeCN/water/TFA mixtures. Yield=37 mg, Rt=2.46 min, MS: 444,(M+H).

Workup

  1. temperatureheated under N2 gas for 18 h
  2. customAt the end of reaction the solvent
  3. customwas removed in vacuo
  4. customwas purified by semi preparative RPHPLC
  5. washeluting with MeCN/water/TFA mixtures

Sources & evidence

ORD record
ord-97ae7df07cf645aeb5d4276c460ffb61
Source dataset
uspto-grants-2007_10
Patent number
US07285558B2

Reaction notes

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