Methanol → HCID 20217523, compound

HRID 235855Notes

Reaction equation

HRID 235855 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([OH:8])=O.[NH2:9][C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[N:13][C:14](Cl)=[CH:15][CH:16]=2)[N:11]=1.[CH3:21][OH:22]>O>[O:22]([C:14]1[N:13]=[C:12]2[C:17]([CH:18]=[CH:19][C:10]([NH:9][C:6]([C:2]3[S:1][CH:5]=[CH:4][CH:3]=3)=[O:8])=[N:11]2)=[CH:16][CH:15]=1)[C:21]1[CH:5]=[CH:4][CH:3]=[CH:2][CH:6]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 107002-Thiophenecarboxylic acidHCID 851997-Chloro-1,8-naphthyridin-2-amine

Product 1

HCID 20217523HCID 20217523, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
4 °C

Procedure

The procedure is similar to that described in Example 1, but starting with 2-thiophenecarboxylic acid (4 g), N,N'-carbonyldiimidazole (5.1 g) and 2-amino-7-chloro-1,8-naphthyridine (7 g). The product produced by precipitation in water (8.8 g; m.p. 175° C.) is dissolved in boiling methanol (150 cc). After 3 hours' cooling at 4° C., the crystallised solid is separated by filtration, washed with methanol (3×10 cc) and dried at 40° C. under reduced pressure (0.067 kPa). N-(7-phenoxy-1,8-naphthyridin-2-yl)-2-thiophenecarboxamide (6 g) is produced, m.p. 176° C.

Workup

  1. dissolutionis dissolved
  2. customthe crystallised solid is separated by filtration
  3. washwashed with methanol (3×10 cc)
  4. customdried at 40° C. under reduced pressure (0.067 kPa)

Sources & evidence

ORD record
ord-531f3cbdc867418698515b208edc406c
Source dataset
uspto-grants-1987_02
Patent number
US04642308

Reaction notes

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