2-Propenoic acid, 2-cyano-3-ethoxy-, ethyl ester → HCID 59784522, compound

HRID 470326Notes

Reaction equation

HRID 470326 reaction equation
CO[C:3]1[CH:4]=[CH:5][C:6]2[C:15]3[N:14]=[C:13]([NH:16][NH2:17])[N:12]=[CH:11][C:10]=3[CH2:9][CH2:8][C:7]=2[CH:18]=1.[CH2:19]([O:21][C:22](=[O:30])[C:23](=[CH:26]OCC)[C:24]#[N:25])[CH3:20]>C(O)(=O)C>[CH2:19]([O:21][C:22]([C:23]1[CH:26]=[N:17][N:16]([C:13]2[N:12]=[CH:11][C:10]3[CH2:9][CH2:8][C:7]4[CH:18]=[CH:3][CH:4]=[CH:5][C:6]=4[C:15]=3[N:14]=2)[C:24]=1[NH2:25])=[O:30])[CH3:20]

Participants

4

Reactant 2

HCID 789432-Propenoic acid, 2-cyano-3-ethoxy-, ethyl esterHCID 670585722-Hydrazinyl-5,6-dihydro-8-methoxybenzo[h]quinazoline

Product 1

HCID 59784522HCID 59784522, compoundYield 45.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of (8-Methoxy-5,6-dihydro-benzo[h]quinazolin-2-yl)-hydrazine (100 mg, 0.41 mM), ethyl(ethoxymethylene)cyanoacetate (76 mg, 0.44 mM) in acetic acid (1 ml) was heated for 16 hr then evaporated. The residue was partitioned between dichloromethane and sodium bicarbonate (sat., 50 ml), the organic phase dried with sodium sulfate, filtered and evaporated to a solid. The solid was triturated with ethyl acetate and isolated via filtration and dried under reduced pressure to afford 5-Amino-1-(5,6-dihydro-benzo[h]quinazolin-2-yl)-1H-pyrazole-4-carboxylic acid ethyl ester (63 mg, 42% yield) as a tan solid. ES-MS MH+ 366.3. 1H NMR (300 MHz, ppm, DMSO-d6): 8.65 (s, 1H), 8.17 (d, 1H), 7.78 (s, 1H), 7.55 (br s, 2H), 7.02 (d, 1H), 6.98 (s, 1H), 4.25 (q, 2H), 3.86 (s, 3H), 2.95 (m, 4H), 1.30 (t, 3H).

Workup

  1. temperaturewas heated for 16 hr
  2. customthen evaporated
  3. customThe residue was partitioned between dichloromethane and sodium bicarbonate (sat., 50 ml)
  4. dry with materialthe organic phase dried with sodium sulfate
  5. filtrationfiltered
  6. customevaporated to a solid
  7. customThe solid was triturated with ethyl acetate
  8. customisolated via filtration
  9. customdried under reduced pressure

Sources & evidence

ORD record
ord-d4ffeaf5605d4cacbc0c910098d8061c
Source dataset
uspto-grants-2014_01
Patent number
US08629147B2

Reaction notes

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