Hydrochloric Acid → HCID 18790723, compound

HRID 1107025Notes

Reaction equation

HRID 1107025 reaction equation
[C:1]([C:3]1[C:4]2[CH2:5][C:6]3[N:11]4[CH:12]=[CH:13][N:14]=[C:10]4[C:9](=[O:15])[NH:8][C:7]=3[C:16]=2[CH:17]=[CH:18][CH:19]=1)#[N:2].FC(F)(F)C(O)=O.[ClH:27]>C(O)(=O)C.CO.[Pd]>[ClH:27].[ClH:27].[NH2:2][CH2:1][C:3]1[C:4]2[CH2:5][C:6]3[N:11]4[CH:12]=[CH:13][N:14]=[C:10]4[C:9](=[O:15])[NH:8][C:7]=3[C:16]=2[CH:17]=[CH:18][CH:19]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 6422Trifluoroacetic acidHCID 18790632HCID 18790632, compound

Product 1

HCID 18790723HCID 18790723, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent2×HCID 887MethanolSolvent

Procedure

A mixture of 0.25 g of 9-cyano-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one, 10 ml of acetic acid, 10 ml of trifluoroacetic acid and 20 mg of 10% palladium-on-charcoal is hydrogenated in an autoclave under a pressure of 50 bar for 20 hours. The suspension is filtered and washed with acetic acid. The filtrate is concentrated to dryness under reduced pressure (15 mm Hg; 2 Kpa) at 40° C. The solid obtained is dissolved in a mixture of 50 ml of acetic acid and 10 ml of concentrated hydrochloric acid and then again concentrated to dryness under reduced pressure (15 mm Hg; 2 kPa) at 40° C. The residue obtained, taken up in 25 ml of methanol, is filtered, then washed with two times 25 ml of isopropyl ether and dried under reduced pressure (1 mm Hg; 0.13 kPa) at 20° C. 0.24 g of 9-aminomethyl-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one dihydrochloride is obtained in the form of a white solid melting above 260° C. (Analysis C14H14C12N4;0% Calculated C: 51.71, H: 4.34, N: 17.23; % Found C: 52.11, H: 4.53, N: 17.04).

Workup

  1. filtrationThe suspension is filtered
  2. washwashed with acetic acid
  3. concentrationThe filtrate is concentrated to dryness under reduced pressure (15 mm Hg; 2 Kpa) at 40° C
  4. customThe solid obtained
  5. concentrationagain concentrated to dryness under reduced pressure (15 mm Hg; 2 kPa) at 40° C
  6. customThe residue obtained
  7. filtrationis filtered
  8. washwashed with two times 25 ml of isopropyl ether
  9. customdried under reduced pressure (1 mm Hg; 0.13 kPa) at 20° C

Sources & evidence

ORD record
ord-85cdc04b193f40769948c1e1d8f2e875
Source dataset
uspto-grants-2000_05
Patent number
US06057454

Reaction notes

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