t-butyl(diphenyl)silyl 3-chloro-4-[(2S)oxiranylmethoxy]phenyl ether → 1-[4-(4-{[(2S)-3-(2-Chloro-4-hydroxy-phenoxy)-2-hydroxy-propylamino]-methyl}-piperidine-1-sulfonyl}-phenyl]-3-(2,5-difluoro-benzyl)-urea

HRID 1634803Notes

Reaction equation

HRID 1634803 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.[Cl:34][C:35]1[CH:36]=[C:37]([O:46][Si](C(C)(C)C)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:38]=[CH:39][C:40]=1[O:41][CH2:42][C@@H:43]1[CH2:45][O:44]1>>[Cl:34][C:35]1[CH:36]=[C:37]([OH:46])[CH:38]=[CH:39][C:40]=1[O:41][CH2:42][C@@H:43]([OH:44])[CH2:45][NH:4][CH2:5][CH:6]1[CH2:7][CH2:8][N:9]([S:12]([C:15]2[CH:16]=[CH:17][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:19][CH:20]=2)(=[O:13])=[O:14])[CH2:10][CH2:11]1

Participants

3

Reactant 2

HCID 23381354t-butyl(diphenyl)silyl 3-chloro-4-[(2S)oxiranylmethoxy]phenyl etherHCID 69999063N-(4-{[4-(aminomethyl)-1-piperidinyl]sulfonyl}phenyl)-N'-(2,5-difluorobenzyl)urea formate

Product 1

HCID 101460711-[4-(4-{[(2S)-3-(2-Chloro-4-hydroxy-phenoxy)-2-hydroxy-propylamino]-methyl}-piperidine-1-sulfonyl}-phenyl]-3-(2,5-difluoro-benzyl)-ureaYield 19.7%

Procedure

N-(4-{[4-(aminomethyl)-1-piperidinyl]sulfonyl}phenyl)-N′-(2,5-difluorobenzyl)urea formate (0.827 g, 1.72 mmol) was reacted with t-butyl(diphenyl)silyl 3-chloro-4-[(2S)oxiranylmethoxy]phenyl ether (0.516 9,1.17 mmol) according to example 37 to give the title compound (0.15 g, 0.23 mmol).

Sources & evidence

ORD record
ord-69df0de30f1f4ceda22eea21c050127f
Source dataset
uspto-grants-2003_01
Patent number
US06506901B2

Reaction notes

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