Dimethylformamide → N-(5-(2,4-bis(benzyloxy)-5-isopropylphenyl)-4-(1-methyl-1H-indol-5-yl)-4H-1,2,4-triazol-3-yl)acetamide

HRID 1962845Notes

Reaction equation

[CH:1]([C:4]1[C:5]([O:40][CH2:41][C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)=[CH:6][C:7]([O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[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]=CC=CC=3)=[N:13][N:14]=2)[CH:9]=1)([CH3:3])[CH3:2].CN(C)C=[O:51].C(C1NC=CN=1)(=O)C>C(OCC)(=O)C>[CH2:33]([O:32][C:7]1[CH:6]=[C:5]([O:40][CH2:41][C:42]2[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=2)[C:4]([CH:1]([CH3:2])[CH3:3])=[CH:9][C:8]=1[C:10]1[N:11]([C:22]2[CH:23]=[C:24]3[C:28](=[CH:29][CH:30]=2)[N:27]([CH3:31])[CH:26]=[CH:25]3)[C:12]([NH:15][C:16](=[O:51])[CH3:21])=[N:13][N:14]=1)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

Conditions

Temperature: 75 °C

Procedure

A flask was charged with [5-(5-Isopropyl-2,4-dibenzyloxy-phenyl)-4-(1-methyl-1H-indol-5-yl)-4H-[1,2,4]triazol-3-yl]-phenyl-amine (0.25 mmol, 136 mg.), dimethylformamide (2 mL), and acetylimidazole (2 eq., 90 mg.), and the reaction was heated at 75° C. for 16 hours. The solution was diluted with ethyl acetate (20 mL) and washed with water (3×10 mL), dried and the product was purified by column chromatography to give N-(5-(2,4-bis(benzyloxy)-5-isopropylphenyl)-4-(1-methyl-1H-indol-5-yl)-4H-1,2,4-triazol-3-yl)acetamide.

Workup

washwashed with water (3×10 mL)
customdried
customthe product was purified by column chromatography

Sources & evidence

ORD record: ord-b576a0b9a18842bda7b566184da0c74a
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08415377B2

Reaction notes

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