Nicotinic Acid → N-(7-methoxy-1,8-naphthyridin-2-yl)-3-pyridylcarboxamide

HRID 235849Notes

Reaction equation

HRID 235849 reaction equation
[C:1]([OH:9])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1.[NH2:10][C:11]1[CH:20]=[CH:19][C:18]2[C:13](=[N:14][C:15]([O:21][CH3:22])=[CH:16][CH:17]=2)[N:12]=1>C(O)CC>[CH3:22][O:21][C:15]1[N:14]=[C:13]2[C:18]([CH:19]=[CH:20][C:11]([NH:10][C:1]([C:2]3[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=3)=[O:9])=[N:12]2)=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 938Nicotinic AcidHCID 217930277-methoxy-1,8-Naphthyridin-2-amine

Product 1

HCID 20217532N-(7-methoxy-1,8-naphthyridin-2-yl)-3-pyridylcarboxamideYield 77.7%

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Conditions

Temperature
4 °C

Procedure

The prccedure is similar to that described in Example 1, but starting with nicotinic acid (7.4 g), N,N'-carbonyldiimidazole (9.7 g) and 2-amino-7-methoxy-1,8-naphthyridine (7 g). After filtration, washing with water and drying, the crystallised solid formed during the reaction (10.3 g; m.p. 245° C.) is dissolved in boiling 1-propanol (900 cc). After being cooled for 3 hours at 4° C., the crystallised solid is separated by filtration, washed with 1-propanol (3×20 cc) and dried at 50° C. under reduced pressure (0.067 kPa). N-(7-methoxy-1,8-naphthyridin-2-yl)-3-pyridylcarboxamide (8.7 g) is produced, m.p. 247° C.

Workup

  1. filtrationAfter filtration
  2. washwashing with water
  3. customdrying
  4. customthe crystallised solid formed during the reaction (10.3 g; m.p. 245° C.)
  5. dissolutionis dissolved
  6. customthe crystallised solid is separated by filtration
  7. washwashed with 1-propanol (3×20 cc)
  8. customdried at 50° C. under reduced pressure (0.067 kPa)

Sources & evidence

ORD record
ord-22955bca694c4e8ab386fa9cc242588c
Source dataset
uspto-grants-1987_02
Patent number
US04642308

Reaction notes

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