2-Morpholinoethylamine → 6-[3-Chloro-4-(2-morpholinoethyl)carbamoylmethoxyphenyl]-5-methyl-4,5-dihydro-1,2,4-triazin-3(2H)-one

HRID 1198906Notes

Reaction equation

HRID 1198906 reaction equation
[Cl:1][C:2]1[CH:14]=[C:13]([C:15]2[CH:16]([CH3:22])[NH:17][C:18](=[O:21])[NH:19][N:20]=2)[CH:12]=[CH:11][C:3]=1[O:4][CH2:5][C:6]([O:8]CC)=O.[NH2:23][CH2:24][CH2:25][N:26]1[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1>O>[Cl:1][C:2]1[CH:14]=[C:13]([C:15]2[CH:16]([CH3:22])[NH:17][C:18](=[O:21])[NH:19][N:20]=2)[CH:12]=[CH:11][C:3]=1[O:4][CH2:5][C:6](=[O:8])[NH:23][CH2:24][CH2:25][N:26]1[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1

Participants

4

Reactant 2

HCID 4082852-MorpholinoethylamineHCID 14370696Ethyl alpha-[2-chloro-4-(2,3,4,5-tetrahydro-5-methyl-3-oxo-1,2,4-triazin-6-yl)phenoxy]acetate

Product 1

HCID 147267386-[3-Chloro-4-(2-morpholinoethyl)carbamoylmethoxyphenyl]-5-methyl-4,5-dihydro-1,2,4-triazin-3(2H)-oneYield 40%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixure of 507 mg of ethyl α-[2-chloro-4-(2,3,4,5-tetrahydro-5-methyl-3-oxo-1,2,4-triazin-6-yl)phenoxy]acetate (prepared as described in Example 5) and 407 mg of N-(2-aminoethyl)morpholine was stirred at 110°-115° C. (bath temperature) for 1 hour. The mixture was cooled and poured into water. The crystals which precipitated were collected by filtration. These crude crystals were recrystallized from a mixture of methanol and ethyl acetate to give 255 mg of the title compound as a white powder melting at 179°-181° C. (with decomposition). The filtrate was extracted with ethyl acetate, dried and concentrated by evaporation under reduced pressure, followed by trituration of the residue with ethyl acetate to give a further 91 mg of the title compound as crystals.

Workup

  1. temperatureThe mixture was cooled
  2. customThe crystals which precipitated
  3. filtrationwere collected by filtration
  4. customThese crude crystals were recrystallized from a mixture of methanol and ethyl acetate

Sources & evidence

ORD record
ord-9310b00234fe4e2a9323bb45b2d9d691
Source dataset
uspto-grants-1990_02
Patent number
US04898862

Reaction notes

Loading…