Ammonia → HCID 54355243, compound

HRID 1247942Notes

Reaction equation

HRID 1247942 reaction equation
[CH:1](=[C:8]1[C:12]2[N:13]=[C:14]3[CH:21]=[CH:20][C:19]([C:22](O)=[O:23])=[CH:18][N:15]3[C:16](=[O:17])[C:11]=2[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O1CCCC1.C(Cl)(=O)OCC.[NH3:36]>O1CCOCC1.C(N(CC)CC)C>[CH:1](=[C:8]1[C:12]2[N:13]=[C:14]3[CH:21]=[CH:20][C:19]([C:22]([NH2:36])=[O:23])=[CH:18][N:15]3[C:16](=[O:17])[C:11]=2[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 8028TetrahydrofuranHCID 10928Ethyl chloroformateHCID 54009854HCID 54009854, compound

Product 1

HCID 54355243HCID 54355243, compound

Reagents, catalysts & solvents 2

HCID 8471TriethylamineSolventHCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
15 °C

Procedure

3-benzylidene-1,2,3,10-tetrahydro-10-oxo-cyclopenta[d]pyrido[1,2-a]pyrimidine-7-carboxylic acid (3.2 g) suspended in dioxane (70 ml) and tetrahydrofurane (30 ml) was reacted with ethyl chlorocarbonate (4.55 g) in the presence of triethylamine (4.05 g) under stirring at 15° C. for 2 hours. Then the reaction mixture was treated with dioxane (200 ml) saturated with gaseous ammonia for 30 minutes under stirring. After dilution with ice water and neutralization with HCl, the precipitate was filtered and purified by washing with dimethylformamide to give 2.52 g of 3-benzylidene-1,2,3,10-tetrahydro-10-oxo-cyclopenta[d]pyrido[1,2-a]pyrimidine-7-carboxamide, m.p. 350°-357° C., NMR (CF3COOD) δ ppm: 3.40 (bs) (4H, C-1 and C-2 protons), 7.60 (m) (6H, =CH-- and phenyl protons), 8.42 (d) (1H, C-5 proton), 9.03 (d d) (1H, C-6 proton), 10.09 (d) (1H, C-8 proton).

Workup

  1. stirringunder stirring
  2. filtrationAfter dilution with ice water and neutralization with HCl, the precipitate was filtered
  3. custompurified
  4. washby washing with dimethylformamide

Sources & evidence

ORD record
ord-34152f0219304074bf9e4c3463e40e45
Source dataset
uspto-grants-1985_06
Patent number
US04521419

Reaction notes

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