Tert-butyl-(4-oxiranylmethoxy-phenoxy)-diphenylsilane → [4-(4-{2-[(2S)-2-Hydroxy-3-(4-hydroxy-phenoxy)-propylamino]-ethyl}-phenylamino)-piperidin-1-yl]-(3-methyl-thiophen-2-yl)-methanone

HRID 1281606Notes

Reaction equation

HRID 1281606 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[CH:24]=[CH:23][C:7]([NH:8][CH:9]2[CH2:14][CH2:13][N:12]([C:15]([C:17]3[S:18][CH:19]=[CH:20][C:21]=3[CH3:22])=[O:16])[CH2:11][CH2:10]2)=[CH:6][CH:5]=1.C([Si]([O:42][C:43]1[CH:48]=[CH:47][C:46]([O:49][CH2:50][CH:51]2[CH2:53][O:52]2)=[CH:45][CH:44]=1)(C1C=CC=CC=1)C1C=CC=CC=1)(C)(C)C>>[OH:52][C@H:51]([CH2:50][O:49][C:46]1[CH:47]=[CH:48][C:43]([OH:42])=[CH:44][CH:45]=1)[CH2:53][NH:1][CH2:2][CH2:3][C:4]1[CH:5]=[CH:6][C:7]([NH:8][CH:9]2[CH2:10][CH2:11][N:12]([C:15]([C:17]3[S:18][CH:19]=[CH:20][C:21]=3[CH3:22])=[O:16])[CH2:13][CH2:14]2)=[CH:23][CH:24]=1

Participants

3

Reactant 2

HCID 12045564Tert-butyl-(4-oxiranylmethoxy-phenoxy)-diphenylsilaneHCID 18173956HCID 18173956, compound

Product 1

HCID 69985899[4-(4-{2-[(2S)-2-Hydroxy-3-(4-hydroxy-phenoxy)-propylamino]-ethyl}-phenylamino)-piperidin-1-yl]-(3-methyl-thiophen-2-yl)-methanoneYield 21.9%

Procedure

{4-[4-(2-Aminoethyl)anilino]-1-piperidinyl}(3-methyl-2-thienyl)methanone (0.174, 0.507 mmol) was reacted with tert-butyl-(4-oxiranylmethoxy-phenoxy)-diphenyl-silane (0.206 g, 0.51 mmol) according to Procedure G to give the title compound (0.083 g, 0.111 mmol).

Sources & evidence

ORD record
ord-0aacfdf3dd90465d80314a9d60993dcf
Source dataset
uspto-grants-2002_09
Patent number
US06451814B1

Reaction notes

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