Potassium Carbonate → N-(4-(5-methyl-1,2,4-oxadiazol-3-yl)-2-(2-phenoxyethylamino)benzyl)-3,5-dimethoxy-4-methylbenzamide

HRID 1296756Notes

Reaction equation

[NH2:1][C:2]1[CH:22]=[C:21]([C:23]2[N:27]=[C:26]([CH3:28])[O:25][N:24]=2)[CH:20]=[CH:19][C:3]=1[CH2:4][NH:5][C:6](=[O:18])[C:7]1[CH:12]=[C:11]([O:13][CH3:14])[C:10]([CH3:15])=[C:9]([O:16][CH3:17])[CH:8]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:36][CH2:37][O:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1>CN(C=O)C>[CH3:28][C:26]1[O:25][N:24]=[C:23]([C:21]2[CH:20]=[CH:19][C:3]([CH2:4][NH:5][C:6](=[O:18])[C:7]3[CH:12]=[C:11]([O:13][CH3:14])[C:10]([CH3:15])=[C:9]([O:16][CH3:17])[CH:8]=3)=[C:2]([NH:1][CH2:36][CH2:37][O:38][C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[CH:22]=2)[N:27]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of compound 1g (38 mg, 0.099 mmol) in DMF was added potassium carbonate (28 mg, 0.20 mmol) and 2-bromoethoxybenzene (20 mg, 0.1 mmol). The reaction mixture was heated at 80° C. in a pressure tube for seven days. During this time, two additional portions of 2-bromoethoxybenzene (20 mg each) were added. The reaction mixture was concentrated and purified by preparative thin layer chromatography in 1:1 hexane/ethyl acetate to give compound 42a. ESI-MS m/e 503.3 (M+1).

Workup

concentrationThe reaction mixture was concentrated
custompurified by preparative thin layer chromatography in 1:1 hexane/ethyl acetate

Sources & evidence

ORD record: ord-acf45c4b6ec84d17842d8af9ce7b3a4c
Source dataset: uspto-grants-2007_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07247654B2

Reaction notes

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