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 76104

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-ca50e995b3fa4a0a90d8e327a12543be
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08835464B2

Linked notes

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