(2S)-2-[(4-fluorophenoxy)methyl]oxirane → N-[4-({4-[4-(2-{[(2S)-3-(2-allylphenoxy)-2-hydroxypropyl]amino}ethyl)anilino]-1-piperidinyl}sulfonyl)phenyl]-N-hexylurea

HRID 1281618Notes

Reaction equation

HRID 1281618 reaction equation
C(O)=O.[NH2:4][CH2:5][CH2:6][C:7]1[CH:38]=[CH:37][C:10]([NH:11][CH:12]2[CH2:17][CH2:16][N:15]([S:18]([C:21]3[CH:26]=[CH:25][C:24]([NH:27][C:28]([NH:30]CCCCCC)=[O:29])=[CH:23][CH:22]=3)(=[O:20])=[O:19])[CH2:14][CH2:13]2)=[CH:9][CH:8]=1.F[C:40]1[CH:50]=[CH:49][C:43]([O:44][CH2:45][C@@H:46]2[CH2:48][O:47]2)=[CH:42][CH:41]=1>>[CH2:7]([C:49]1[CH:50]=[CH:40][CH:41]=[CH:42][C:43]=1[O:44][CH2:45][C@@H:46]([OH:47])[CH2:48][NH:4][CH2:5][CH2:6][C:7]1[CH:8]=[CH:9][C:10]([NH:11][CH:12]2[CH2:17][CH2:16][N:15]([S:18]([C:21]3[CH:22]=[CH:23][C:24]([N:27]([CH2:25][CH2:26][CH2:21][CH2:22][CH2:23][CH3:24])[C:28]([NH2:30])=[O:29])=[CH:25][CH:26]=3)(=[O:20])=[O:19])[CH2:14][CH2:13]2)=[CH:37][CH:38]=1)[CH:6]=[CH2:5]

Participants

3

Reactant 2

HCID 6932898(2S)-2-[(4-fluorophenoxy)methyl]oxiraneHCID 69985670N-[4-([4-[4-(2-Aminoethyl)anilino]-1-piperidinyl}sulfonyl)phenyl]-N'-hexylurea formate

Product 1

HCID 70133387N-[4-({4-[4-(2-{[(2S)-3-(2-allylphenoxy)-2-hydroxypropyl]amino}ethyl)anilino]-1-piperidinyl}sulfonyl)phenyl]-N-hexylureaYield 36.9%

Procedure

N-[4-({4-[4-(2-Aminoethyl)anilino]-1-piperidinyl}sulfonyl)phenyl]-N′-hexylurea formate (0.172 g 0.314 mmol) was reacted (2S)-2-[(4-fluorophenoxy)methyl]oxirane (0.06 g, 0.315 mmol) according to Procedure G to give the title compound (0.04 g, 0.058 mmol).

Sources & evidence

ORD record
ord-a5ea2c4512ce4399891cf519be0ffbf4
Source dataset
uspto-grants-2002_09
Patent number
US06451814B1

Reaction notes

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