Tert-butyl-(4-oxiranylmethoxy-phenoxy)-diphenylsilane → 1-(2,5-Difluoro-benzyl)-3-[4-(4-{[(2S)-2-hydroxy-3-(4-hydroxy-phenoxy)-propylamino]-methyl}-piperidine-1-sulfonyl)-phenyl]-urea

HRID 1634800Notes

Reaction equation

HRID 1634800 reaction equation
C(O)=O.[NH2:4][CH2:5][CH:6]1[CH2:11][CH2:10][N:9]([S:12]([C:15]2[CH:20]=[CH:19][C:18]([NH:21][C:22]([NH:24][CH2:25][C:26]3[CH:31]=[C:30]([F:32])[CH:29]=[CH:28][C:27]=3[F:33])=[O:23])=[CH:17][CH:16]=2)(=[O:14])=[O:13])[CH2:8][CH2:7]1.C([Si]([O:51][C:52]1[CH:57]=[CH:56][C:55]([O:58][CH2:59][CH:60]2[CH2:62][O:61]2)=[CH:54][CH:53]=1)(C1C=CC=CC=1)C1C=CC=CC=1)(C)(C)C>>[F:33][C:27]1[CH:28]=[CH:29][C:30]([F:32])=[CH:31][C:26]=1[CH2:25][NH:24][C:22]([NH:21][C:18]1[CH:17]=[CH:16][C:15]([S:12]([N:9]2[CH2:8][CH2:7][CH:6]([CH2:5][NH:4][CH2:62][C@H:60]([OH:61])[CH2:59][O:58][C:55]3[CH:56]=[CH:57][C:52]([OH:51])=[CH:53][CH:54]=3)[CH2:11][CH2:10]2)(=[O:13])=[O:14])=[CH:20][CH:19]=1)=[O:23]

Participants

3

Reactant 2

HCID 12045564Tert-butyl-(4-oxiranylmethoxy-phenoxy)-diphenylsilaneHCID 69999063N-(4-{[4-(aminomethyl)-1-piperidinyl]sulfonyl}phenyl)-N'-(2,5-difluorobenzyl)urea formate

Product 1

HCID 101454821-(2,5-Difluoro-benzyl)-3-[4-(4-{[(2S)-2-hydroxy-3-(4-hydroxy-phenoxy)-propylamino]-methyl}-piperidine-1-sulfonyl)-phenyl]-ureaYield 13%

Procedure

N-(4-{[4-(aminomethyl)-1-piperidinyl]sulfonyl}phenyl)-N′-(2,5-difluorobenzyl)urea formate (0.433 g, 1.00 mmol) was reacted with t-butyl-(4-oxiranylmethoxy-phenoxy)-diphenyl-silane (0.404 g, 1.00 mmol) according to example 37 to give the title compound (0.084 g, 0.13 mmol).

Sources & evidence

ORD record
ord-e12e2ef0fc6a4831986eea91e64c172e
Source dataset
uspto-grants-2003_01
Patent number
US06506901B2

Reaction notes

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