Water → HCID 20217536, compound

HRID 235823Notes

Reaction equation

HRID 235823 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=O)=[CH:5][CH:4]=1.[NH2:12][C:13]1[CH:22]=[CH:21][C:20]2[C:15](=[N:16][C:17]([O:23][CH:24]([CH3:26])[CH3:25])=[CH:18][CH:19]=2)[N:14]=1.O.C(OC(C)C)(C)C>C(OCC)C>[CH:24]([O:23][C:17]1[N:16]=[C:15]2[C:20]([CH:21]=[CH:22][C:13]([NH:12][C:7](=[O:9])[C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:11][CH:10]=3)=[N:14]2)=[CH:19][CH:18]=1)([CH3:26])[CH3:25]

Participants

6

Reactant 4

HCID 962WaterHCID 74784-Methoxybenzoic AcidHCID 7914Diisopropyl EtherHCID 20217529HCID 20217529, compound

Product 1

HCID 20217536HCID 20217536, compoundYield 34.8%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
4 °C

Procedure

The procedure is similar to that described in Example 1, but starting with 4-methoxybenzoic acid (16.7 g), N,N'-carbonyldiimidazole (19.4 g) and 2-amino-7-isopropoxy-1,8-naphthyridine (25 g). The reaction mixture is poured into water and extracted with ethyl acetate. After concentration to dryness under reduced pressure (4 kPa), the oil produced (39 g) is stirred in the presence of diethyl ether (100 cc) to give a crystallised solid (23 g; m.p. 78° C.). The product produced is dissolved in boiling isopropyl ether (100 cc). After 2 hours' cooling at 4° C., the crystallised solid is separated by filtration, washed with diethyl ether (2×10 cc) and dried at 40° C. under reduced pressure (0.067 kPa). N-(7-isopropoxy-1,8-naphthyridin-2-yl)-4-methoxybenzamide (12.9 g) is produced, m.p. 82° C.

Workup

  1. extractionextracted with ethyl acetate
  2. concentrationAfter concentration to dryness under reduced pressure (4 kPa)
  3. customthe oil produced (39 g)
  4. customto give a crystallised solid (23 g; m.p. 78° C.)
  5. customThe product produced
  6. dissolutionis dissolved
  7. customthe crystallised solid is separated by filtration
  8. washwashed with diethyl ether (2×10 cc)
  9. customdried at 40° C. under reduced pressure (0.067 kPa)

Sources & evidence

ORD record
ord-9444b80d153d46b2aab5d74bac2cfa53
Source dataset
uspto-grants-1987_02
Patent number
US04642308

Reaction notes

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