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

HRID 1634801Notes

Reaction equation

HRID 1634801 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.[F:34][C:35]1[CH:40]=[C:39]([O:41][CH2:42][C@@H:43]2[CH2:45][O:44]2)[CH:38]=[CH:37][C:36]=1[O:46][Si](C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1>>[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][CH2:45][C@H:43]([OH:44])[CH2:42][O:41][C:39]3[CH:38]=[CH:37][C:36]([OH:46])=[C:35]([F:34])[CH:40]=3)[CH2:11][CH2:10]2)(=[O:13])=[O:14])=[CH:20][CH:19]=1)=[O:23]

Participants

3

Reactant 2

HCID 23381349t-Butyl{2-fluoro-4-[(2s)oxiranylmethoxy]phenoxy}diphenylsilaneHCID 69999063N-(4-{[4-(aminomethyl)-1-piperidinyl]sulfonyl}phenyl)-N'-(2,5-difluorobenzyl)urea formate

Product 1

HCID 103045651-(2,5-Difluoro-benzyl)-3-[4-(4-{[(2S)-3-(3-fluoro-4-hydroxy-phenoxy)-2-hydroxy-propylamino]-methyl}-piperidine-1-sulfonyl)-phenyl]-ureaYield 16%

Procedure

N-(4-{[4-(aminomethyl)-1-piperidinyl]sulfonyl}phenyl)-N′-(2,5-difluoro-benzyl)urea formate (0.433 g, 1.00 mmol) was reacted with t-butyl(diphenyl)silyl 2-fluoro-4-[(2S)oxiranylmethoxy]phenyl ether (0.422 g, 1.00 mmol) according to example 37 to give the title compound (0.1 g, 0.16 mmol).

Sources & evidence

ORD record
ord-6a9bab214f07407ca1b88dd387189080
Source dataset
uspto-grants-2003_01
Patent number
US06506901B2

Reaction notes

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