5-Methylthiophene-2-carboxylic acid → HCID 13579415, compound

HRID 235857Notes

Reaction equation

HRID 235857 reaction equation
[CH3:1][C:2]1[S:6][C:5]([C:7]([OH:9])=O)=[CH:4][CH:3]=1.[NH2:10][C:11]1[CH:20]=[CH:19][C:18]2[C:13](=[N:14][C:15]([Cl:21])=[CH:16][CH:17]=2)[N:12]=1>C(#N)C>[Cl:21][C:15]1[N:14]=[C:13]2[C:18]([CH:19]=[CH:20][C:11]([NH:10][C:7]([C:5]3[S:6][C:2]([CH3:1])=[CH:3][CH:4]=3)=[O:9])=[N:12]2)=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 747135-Methylthiophene-2-carboxylic acidHCID 851997-Chloro-1,8-naphthyridin-2-amine

Product 1

HCID 13579415HCID 13579415, compoundYield 37.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
4 °C

Procedure

The procedure is identical to that described in Example 1, but starting with 5-methylthiophene-2-carboxylic acid (4.1 g), N,N'-carbonyldiimidazole (5.6 g) and 2-amino-7-chloro-1,8-naphthyridine (4.85 g). The product produced (3.8 g; m.p. 220° C.) is dissolved in boiling acetonitrile (150 cc). After 4 hours' cooling at 4° C., the crystallised solid is separated by filtration, washed with acetonitrile (2×10 cc) and dried at 40° C. under reduced pressure (0.066 kPa). N-(7-Chloro-1,8-naphthyridin-2-yl)-5-methylthiophene-2-carboxamide (3.1 g) is produced, m.p. 222° C.

Workup

  1. customThe product produced (3.8 g; m.p. 220° C.)
  2. dissolutionis dissolved
  3. customthe crystallised solid is separated by filtration
  4. washwashed with acetonitrile (2×10 cc)
  5. customdried at 40° C. under reduced pressure (0.066 kPa)

Sources & evidence

ORD record
ord-da368188593048c49b4aafd9b52616a7
Source dataset
uspto-grants-1987_02
Patent number
US04642308

Reaction notes

Loading…