Ammonium Chloride → 4-Isopropyl-6-[4-(1-methyl-1H-indol-5-yl)-5-phenylamino-4H-[1,2,4]triazol-3-yl]-benzene-1,3-diol

HRID 555947Notes

Reaction equation

[CH:1]([C:4]1[C:5]([O:34]C)=[CH:6][C:7]([O:32]C)=[C:8]([C:10]2[N:11]([C:22]3[CH:23]=[C:24]4[C:28](=[CH:29][CH:30]=3)[N:27]([CH3:31])[CH:26]=[CH:25]4)[C:12]([NH:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[N:13][N:14]=2)[CH:9]=1)([CH3:3])[CH3:2].[Cl-].[NH+]1C=CC=CC=1.[Cl-].[NH4+]>ClCCl>[CH:1]([C:4]1[CH:9]=[C:8]([C:10]2[N:11]([C:22]3[CH:23]=[C:24]4[C:28](=[CH:29][CH:30]=3)[N:27]([CH3:31])[CH:26]=[CH:25]4)[C:12]([NH:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[N:13][N:14]=2)[C:7]([OH:32])=[CH:6][C:5]=1[OH:34])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 210 °C

Procedure

A flask was charged with [5-(5-Isopropyl-2,4-dimethoxy-phenyl)-4-(1-methyl-1H-indol-5-yl)-4H-[1,2,4]triazol-3-yl]-phenyl-amine (27 mg; 0.06 mmol) and pyridinium chloride (2 g.). The reactants were placed under a nitrogen atmosphere, and the reaction was heated to 210° C. for 25 minutes. To the cooled reaction mixture was added dichloromethane and saturated ammonium chloride solution. The organic fraction was isolated, and the product was purified by column chromatography to give 4-Isopropyl-6-[4-(1-methyl-1H-indol-5-yl)-5-phenylamino-4H-[1,2,4]triazol-3-yl]-benzene-1,3-diol (18 mg; 0.04 mmol.)

Workup

customTo the cooled reaction mixture
customThe organic fraction was isolated
customthe product was purified by column chromatography

Sources & evidence

ORD record: ord-f155945adeb0442fbbe64c92144e2efd
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08053456B2

Reaction notes

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