Aniline → HCID 18790690, compound

HRID 1107024Notes

Reaction equation

HRID 1107024 reaction equation
[O:1]=[C:2]1[NH:7][C:6]2[C:8]3[CH:9]=[CH:10][CH:11]=[C:12]([CH2:15][C:16]([OH:18])=O)[C:13]=3[CH2:14][C:5]=2[N:4]2[CH:19]=[CH:20][N:21]=[C:3]12.Cl.CN(C)CCCN=C=NCC.O[C:35]1[C:43]2N=N[NH:40][C:39]=2[CH:38]=[CH:37][CH:36]=1.NC1C=CC=CC=1.C(=O)([O-])O.[Na+]>CN(C)C=O.Cl.O>[C:39]1([NH:40][C:16](=[O:18])[CH2:15][C:12]2[C:13]3[CH2:14][C:5]4[N:4]5[CH:19]=[CH:20][N:21]=[C:3]5[C:2](=[O:1])[NH:7][C:6]=4[C:8]=3[CH:9]=[CH:10][CH:11]=2)[CH:43]=[CH:35][CH:36]=[CH:37][CH:38]=1

Participants

9

Reactant 5

HCID 6115AnilineHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 9838629HCID 9838629, compoundHCID 178418300HCID 178418300, compound

Product 1

HCID 18790690HCID 18790690, compoundYield 28.2%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolvent2×HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 0.56 g of (4,5-dihydro-4-oxo-10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-9-yl)acetic acid, 0.38 g of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, 0.27 g of hydroxybenzotriazole and 1.1 ml of aniline in 20 ml of dimethylformamide is stirred under an argon atmosphere for 20 hours at a temperature in the region of 20° C. 20 ml of hydrochloric acid are added to the reaction mixture. The precipitate formed is filtered, washed with water and with isopropyl ether and then dried under reduced pressure (15 mm Hg; 2 kPa) at 20° C. The beige solid obtained is suspended in a solution of 20 ml of water and 84 mg of sodium hydrogencarbonate and then filtered and washed with water. The solid obtained is resuspended in 10 ml of 0.1N hydrochloric acid and then filtered, washed with water and dried under reduced pressure (1 mm Hg; 0.13 kPa) at 60° C. 0.2 g of N-phenyl-2-(4,5-dihydro-4-oxo-10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-9-yl)acetamide is obtained in the form of a white solid melting at a temperature greater than 260° C. (Analysis C21H16N402; % Calculated C: 70.77, H: 4.53, N: 15.72; % Found C: 70.74, H: 4.39, N: 15.64).

Workup

  1. customThe precipitate formed
  2. filtrationis filtered
  3. washwashed with water and with isopropyl ether
  4. customdried under reduced pressure (15 mm Hg; 2 kPa) at 20° C
  5. customThe beige solid obtained
  6. filtrationfiltered
  7. washwashed with water
  8. customThe solid obtained
  9. filtrationfiltered
  10. washwashed with water
  11. customdried under reduced pressure (1 mm Hg; 0.13 kPa) at 60° C

Sources & evidence

ORD record
ord-d9c18f74ac0c4bb38e201606c7ec97b4
Source dataset
uspto-grants-2000_05
Patent number
US06057454

Reaction notes

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