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

HRID 1281601Notes

Reaction equation

HRID 1281601 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[CH:29]=[CH:28][C:7]([NH:8][CH:9]2[CH2:14][CH2:13][N:12]([C:15]([C:17]3[S:18][C:19]4[CH:27]=[CH:26][CH:25]=[CH:24][C:20]=4[C:21]=3[O:22][CH3:23])=[O:16])[CH2:11][CH2:10]2)=[CH:6][CH:5]=1.C([Si]([O:47][C:48]1[CH:53]=[CH:52][C:51]([O:54][CH2:55][CH:56]2[CH2:58][O:57]2)=[CH:50][CH:49]=1)(C1C=CC=CC=1)C1C=CC=CC=1)(C)(C)C>>[OH:57][C@H:56]([CH2:55][O:54][C:51]1[CH:52]=[CH:53][C:48]([OH:47])=[CH:49][CH:50]=1)[CH2:58][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][C:19]4[CH:27]=[CH:26][CH:25]=[CH:24][C:20]=4[C:21]=3[O:22][CH3:23])=[O:16])[CH2:13][CH2:14]2)=[CH:28][CH:29]=1

Participants

3

Reactant 2

HCID 12045564Tert-butyl-(4-oxiranylmethoxy-phenoxy)-diphenylsilaneHCID 18174005{4-[4-(2-Aminoethyl)anilino]-1-piperidinyl}(3-methoxy-1-benzothiophen-2-yl)methanone

Product 1

HCID 10188304[4-(4-{2-[(2S)-2-Hydroxy-3-(4-hydroxy-phenoxy)-propylamino]-ethyl}-phenylamino)-piperidin-1-yl]-(3-methoxy-benzo[b]thiophen-2-yl)-methanoneYield 30.6%

Procedure

{4-[4-(2-Aminoethyl)anilino]-1-piperidinyl}(3-methoxy-1-benzothiophen-2-yl)methanone (0.189 g, 0.461 mmol) was reacted with tert-butyl-(4-oxiranylmethoxy-phenoxy)-diphenyl-silane (0.187 g, 0.461 mmol) according to Procedure G to give the title compound (0.119 g, 0.141 mmol).

Sources & evidence

ORD record
ord-e6be8b8434714cb68f1e801e544d91ad
Source dataset
uspto-grants-2002_09
Patent number
US06451814B1

Reaction notes

Loading…