N-methyl-2-pyrrolidone → HCID 13824495, compound

HRID 542518Notes

Reaction equation

HRID 542518 reaction equation
Br[C:2]1[N:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6](=[O:12])[NH:7]2.[CH3:13][C:14]1[CH:18]=[CH:17][NH:16][N:15]=1.CN1CCCC1=O>O>[CH3:13][C:14]1[CH:18]=[CH:17][N:16]([C:2]2[N:11]=[CH:10][CH:9]=[C:8]3[C:3]=2[CH:4]=[CH:5][C:6](=[O:12])[NH:7]3)[N:15]=1

Participants

5

Reactant 3

HCID 13387N-methyl-2-pyrrolidoneHCID 117758245-Bromo-1,6-naphthyridin-2(1H)-one2×HCID 178428694HCID 178428694, compound

Product 1

HCID 13824495HCID 13824495, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
200 °C

Procedure

A stirred mixture containing 13.5 g of 5-bromo-1,6-naphthyridin-2(1H)-one, 18 ml of 3-methyl-1H-pyrazole and 75 ml of N-methylpyrrolidinone was heated in an oil bath at 170°-180° C. for 18 hours, after which a tlc analysis indicated some remaining starting material. The temperature of the oil bath was raised to 200° C.; and, the reaction mixture was heated for an additional 5 hours and then poured into water. The solid that separated was collected, dried and combined with 1.7 g of corresponding material obtained in another run starting with 2.25 g of 5-bromo-1,6-naphthyridin-2(1H)-one. The combined solids were recrystallized from dimethylformamide and dried in an oven for three days at 100° C. to yield 6.6 g of 5-(3-methyl-1H-pyrazol-1-yl)-1,6-naphthyridin-2(1H)-one, m.p. >300° C.

Workup

  1. temperaturewas heated in an oil bath at 170°-180° C. for 18 hours
  2. temperatureand, the reaction mixture was heated for an additional 5 hours
  3. customThe solid that separated
  4. customwas collected
  5. customdried
  6. customobtained in another run
  7. customThe combined solids were recrystallized from dimethylformamide
  8. customdried in an oven for three days at 100° C.

Sources & evidence

ORD record
ord-1c58067a0e4b4ff6b6f7b248eb27a835
Source dataset
uspto-grants-1987_04
Patent number
US04657915

Reaction notes

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