Diisopropylethylamine → HCID 16723003, compound

HRID 1983161Notes

Reaction equation

HRID 1983161 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]([C:13]3[C:14]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)=[N:15][O:16][C:17]=3[CH:18]3[CH2:20][CH2:19]3)=[N:11][N:12]=2)=[C:4]([O:27][CH3:28])[CH:3]=1.[NH2:29][CH:30]1[CH2:35][CH2:34][O:33][CH2:32][CH2:31]1.C(N(CC)C(C)C)(C)C>>[CH:18]1([C:17]2[O:16][N:15]=[C:14]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:13]=2[C:10]2[O:9][C:8]([C:5]3[CH:6]=[CH:7][C:2]([NH:29][CH:30]4[CH2:35][CH2:34][O:33][CH2:32][CH2:31]4)=[CH:3][C:4]=3[O:27][CH3:28])=[N:12][N:11]=2)[CH2:20][CH2:19]1

Participants

4

Reactant 3

HCID 81531DiisopropylethylamineHCID 4192234-AminotetrahydropyranHCID 16722950HCID 16722950, compound

Product 1

HCID 16723003HCID 16723003, compoundYield 35%

Procedure

As described for example 26, 2-(4-fluoro-2-methoxy-phenyl)-5-(5-cyclopropyl-3-phenyl-isoxazol-4-yl)-[1,3,4]oxadiazole (200 mg, 0.53 mmol) instead of 2-(4-fluoro-2-methoxy-phenyl)-5-(5-methyl-3-phenyl-isoxazol-4-yl)-[1,3,4]oxadiazole was converted using 4-aminotetrahydropyran (161 mg, 1.59 mmol) and N,N-diisopropylethylamine (137 mg, 1.06 mmol) instead of thiomorpholine to the title compound (SiO2, heptane:ethyl acetate:dichloromethane:methanol=40:40:20:0 to 0:75:20:5, 84 mg, 35%) which was obtained as a white solid. MS: m/e=459.4 [M+H]+.

Sources & evidence

ORD record
ord-c39efd99d5ac423cb653fda8a9210803
Source dataset
uspto-grants-2009_06
Patent number
US07541372B2

Reaction notes

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