N-(4-{[4-(aminomethyl)-1-piperidinyl]sulfonyl}phenyl)-N'-(2,5-difluorobenzyl)urea formate → N-(5-{(2S)-3-[(1-{4-[3-(2,5-Difluoro-benzyl)-ureido]-benzenesulfonyl}-piperidin-4-ylmethyl)-amino]-2-hydroxy-propoxy}-2-hydroxy-phenyl)-methanesulfonamide

HRID 1634802Notes

Reaction equation

HRID 1634802 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.[Si]([O:51][C:52]1[CH:57]=[CH:56][C:55]([O:58][CH2:59][C@@H:60]2[CH2:62][O:61]2)=[CH:54][C:53]=1[N:63]([S:67]([CH3:70])(=[O:69])=[O:68])C(=O)[O-])(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](=[O:23])[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])=[C:53]([NH:63][S:67]([CH3:70])(=[O:69])=[O:68])[CH:54]=3)[CH2:11][CH2:10]2)(=[O:13])=[O:14])=[CH:20][CH:19]=1

Participants

3

Reactant 2

HCID 69999063N-(4-{[4-(aminomethyl)-1-piperidinyl]sulfonyl}phenyl)-N'-(2,5-difluorobenzyl)urea formateHCID 867587982-{[t-butyl(diphenyl)silyl]oxy}-5-[(2S)oxiranylmethoxy]phenyl(methylsulfonyl)carbamate

Product 1

HCID 10283539N-(5-{(2S)-3-[(1-{4-[3-(2,5-Difluoro-benzyl)-ureido]-benzenesulfonyl}-piperidin-4-ylmethyl)-amino]-2-hydroxy-propoxy}-2-hydroxy-phenyl)-methanesulfonamideYield 7.5%

Procedure

N-(4-{[4-(aminomethyl)-1-piperidinyl]sulfonyl}phenyl)-N′-(2,5-difluorobenzyl)urea formate (0.285 g, 0.535 mmol) was reacted with 2-{[t-butyl(diphenyl)silyl]oxy}-5-[(2S)oxiranylmethoxy]phenyl(methylsulfonyl)carbamate (0.322 g, 0.535 mmol) according to example 37 to give the title compound (0.03 g, 0.04 mmol).

Sources & evidence

ORD record
ord-8e4b9056d6dc497597b387d0c59d9b4c
Source dataset
uspto-grants-2003_01
Patent number
US06506901B2

Reaction notes

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