Potassium Phosphate, Tribasic → 6-[[6-(Acetylamino)-pyrimidin-4-yl]oxy]-naphthalene-1-carboxylic acid [3-(4-methyl-imidazol-1-yl)-5-trifluoromethyl-phenyl]-amide

HRID 1512193Notes

Reaction equation

HRID 1512193 reaction equation
P([O-])([O-])([O-])=O.[K+].[K+].[K+].[OH:9][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[C:16]([C:20]([NH:22][C:23]1[CH:28]=[C:27]([C:29]([F:32])([F:31])[F:30])[CH:26]=[C:25]([N:33]3[CH:37]=[C:36]([CH3:38])[N:35]=[CH:34]3)[CH:24]=1)=[O:21])=[CH:15][CH:14]=[CH:13]2.Cl[C:40]1[N:45]=[CH:44][N:43]=[C:42]([NH:46][C:47](=[O:49])[CH3:48])[CH:41]=1>C1(C)C=CC=CC=1>[CH3:38][C:36]1[N:35]=[CH:34][N:33]([C:25]2[CH:24]=[C:23]([NH:22][C:20]([C:16]3[C:17]4[C:12](=[CH:11][C:10]([O:9][C:40]5[CH:41]=[C:42]([NH:46][C:47](=[O:49])[CH3:48])[N:43]=[CH:44][N:45]=5)=[CH:19][CH:18]=4)[CH:13]=[CH:14][CH:15]=3)=[O:21])[CH:28]=[C:27]([C:29]([F:30])([F:31])[F:32])[CH:26]=2)[CH:37]=1

Participants

5

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 539477N-(6-chloropyrimidin-4-yl)acetamideHCID 68591664HCID 68591664, compound

Product 1

HCID 251573116-[[6-(Acetylamino)-pyrimidin-4-yl]oxy]-naphthalene-1-carboxylic acid [3-(4-methyl-imidazol-1-yl)-5-trifluoromethyl-phenyl]-amide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

Anhydrous tripotassium phosphate (848 mg, 4.0 mmol) is added to a stirred solution of 6-hydroxy-N-[3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl]-1-naphthalenecarboxamide (411 mg, 1.0 mmol) in toluene (40 mL) under an argon atmosphere at 110° C. N-(6-Chloro-4-pyrimidinyl)-acetamide (252 mg, 1.5 mmol) is added and the mixture is stirred at 110° C. for a further 50 hours. The solvent is evaporated off under reduced pressure and the residue is washed with a saturated aqueous solution of NH4Cl and dried. The crude product is purified by recrystallisation from methanol to afford the title compound as a beige solid, m.p.: 291-293° C.

Workup

  1. customThe solvent is evaporated off under reduced pressure
  2. washthe residue is washed with a saturated aqueous solution of NH4Cl
  3. customdried
  4. customThe crude product is purified by recrystallisation from methanol

Sources & evidence

ORD record
ord-7f97b7ddad0041b4ba448616deaa80a4
Source dataset
uspto-grants-2012_07
Patent number
US08217045B2

Reaction notes

Loading…