Acetic Anhydride → HCID 23154959, compound

HRID 1912779Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:30])[NH:10][C:11]2[CH:16]=[CH:15][C:14]([N:17]3[C:25]4[C:20](=[CH:21][C:22]([C:26]([NH:28][OH:29])=[NH:27])=[CH:23][CH:24]=4)[CH:19]=[CH:18]3)=[CH:13][CH:12]=2)=[CH:4][C:3]=1[C:31]([F:34])([F:33])[F:32].[C:35](OC(=O)C)(=O)[CH3:36]>N1C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([NH:10][C:11]2[CH:12]=[CH:13][C:14]([N:17]3[C:25]4[C:20](=[CH:21][C:22]([C:26]5[N:27]=[C:35]([CH3:36])[O:29][N:28]=5)=[CH:23][CH:24]=4)[CH:19]=[CH:18]3)=[CH:15][CH:16]=2)=[O:30])=[CH:4][C:3]=1[C:31]([F:34])([F:32])[F:33]

Participants

Conditions

Temperature: 80 °C

Procedure

In 0.2 mL of pyridine, 10.5 mg (0.022 mmol) of 1-{4-[3-(4-chloro-3-(trifluoromethyl)phenyl)ureido]phenyl}-N-hydroxy-1H-indole-5-carboxamidine was dissolved, and 10 mg (0.098 mmol) of acetic anhydride was added thereto, and the mixture solution was stirred at 80° C. for 14 hours. The reaction solution was concentrated under reduced pressure, and then the obtained residue was purified by Megabond Elute Silica Gel (a product of Varian, 1 g, methylene chloride:methanol=20:1) to obtain 4.1 mg (37%) of 1-(4-chloro-3-(trifluoromethyl)phenyl)-3-{4-[5-(5-methyl-[1,2,4]oxadiazol-3-yl)indol-1-yl]phenyl}urea (Table 1, Compound No. 26).

Workup

concentrationThe reaction solution was concentrated under reduced pressure
customthe obtained residue was purified by Megabond
washElute Silica Gel (a product of Varian, 1 g, methylene chloride

Sources & evidence

ORD record: ord-eb33aab83982460581ae5ead52a7a5f4
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08609656B2

Reaction notes

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