Ammonium Chloride → HCID 11245159, compound

HRID 558334Notes

Reaction equation

HRID 558334 reaction equation
[F:1][C:2]([F:25])([F:24])[O:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:23])[C:12]2[CH:13]=[C:14]([CH:18]=[CH:19][C:20]=2[O:21][CH3:22])[C:15](O)=[O:16])=[CH:6][CH:5]=1.[Cl-].[NH4+].O.[N:29]1(O)C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.C(N(CC)C(C)C)(C)C>CN(C)C=O>[F:1][C:2]([F:25])([F:24])[O:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:23])[C:12]2[CH:13]=[C:14]([CH:18]=[CH:19][C:20]=2[O:21][CH3:22])[C:15]([NH2:29])=[O:16])=[CH:6][CH:5]=1

Participants

7

Reactant 5

HCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 23141413HCID 23141413, compound

Product 1

HCID 11245159HCID 11245159, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-(4-Trifluoromethoxyphenyl)-4-methoxyisophthalamic acid (48 mg) obtained in step F, 11 mg of ammonium chloride, 25 mg of benzotriazol-1-ol monohydrate, and 31 mg of (3-dimethylaminopropyl)ethylcarbodiimide hydrochloride were dissolved in 2 mL of N,N-dimethylformamide, and 70 μL of N,N-diisopropylethylamine was added. This solution was stirred overnight at room temperature, and then the solvent was distilled off under reduced pressure. The resulting residue was purified by column chromatography (5 g of silica gel, 2 g of aminopropyl-modified silica gel) using a 100:1 mixture of dichloromethane and methanol as an elution solvent, thereby obtaining 45 mg (96%) of 3-N-(4-trifluoromethoxyphenyl)-4-methoxyisophthalamide.

Workup

  1. distillationthe solvent was distilled off under reduced pressure
  2. customThe resulting residue was purified by column chromatography (5 g of silica gel, 2 g of aminopropyl-modified silica gel)
  3. additiona 100:1 mixture of dichloromethane and methanol as an elution solvent

Sources & evidence

ORD record
ord-72fc2f7e976f42999ce6670c9c0793cb
Source dataset
uspto-grants-2011_11
Patent number
US08063046B2

Reaction notes

Loading…