Methylamine → HCID 18790704, compound

HRID 1107023Notes

Reaction equation

HRID 1107023 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.[CH3:22][NH2:23]>C(O)C.CO.CC(C)=O>[CH3:22][NH:23][C:16](=[O:18])[CH2:15][C:12]1[C:13]2[CH2:14][C:5]3[N:4]4[CH:19]=[CH:20][N:21]=[C:3]4[C:2](=[O:1])[NH:7][C:6]=3[C:8]=2[CH:9]=[CH:10][CH:11]=1

Participants

6

Reactant 2

HCID 6329MethylamineHCID 9838629HCID 9838629, compound

Product 1

HCID 18790704HCID 18790704, compound

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 702EthanolSolventHCID 887MethanolSolvent2×

Procedure

A solution of 0.93 g of the ethyl ester of (4,5-dihydro-4-oxo-10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-9-yl)acetic acid, 20 ml of methylamine as a 33% solution in ethanol and 20 ml of methanol under an argon atmosphere is stirred at a temperature in the region of 20° C. for 18 hours. The reaction mixture is filtered. The precipitate obtained is washed successively with three times 40 ml of ethanol and three times 40 ml of methyl-tert-butyl ether and dried under reduced pressure (15 mm Hg; 2 kPa) at 20° C. The solid obtained is suspended in a mixture of acetone (25 ml) and methanol (5 ml) and stirred for 15 minutes and then filtered, washed with 10 ml of acetone and dried under reduced pressure (1 mm Hg; 0.13 kPa) at 60° C. 0.32 g of N-methyl-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, the melting point of which is greater than 260° C. (Analysis C16H14N4O2; % Calculated C: 65.30, H: 4.79, N: 19.04; % Found C: 65.00, H: 4.50, N: 18.80).

Workup

  1. filtrationThe reaction mixture is filtered
  2. customThe precipitate obtained
  3. washis washed successively with three times 40 ml of ethanol and three times 40 ml of methyl-tert-butyl ether
  4. customdried under reduced pressure (15 mm Hg; 2 kPa) at 20° C
  5. customThe solid obtained
  6. filtrationfiltered
  7. washwashed with 10 ml of acetone
  8. customdried under reduced pressure (1 mm Hg; 0.13 kPa) at 60° C

Sources & evidence

ORD record
ord-462cf64f7cb6430a8901f044cda0695a
Source dataset
uspto-grants-2000_05
Patent number
US06057454

Reaction notes

Loading…