1-chloro-6-(1-hydroxy-2-methyl-1-(1-trityl-1H-imidazol-4-yl)propyl)-2-naphthoic acid → 1-Chloro-6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl)-2-naphthamide

HRID 480492Notes

Reaction equation

HRID 480492 reaction equation
ClC1C2C(=CC(C(O)(C3[N:17]=CN(C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)C=3)C(C)C)=CC=2)C=CC=1C(OC)=O.[Cl:45][C:46]1[C:55]2[C:50](=[CH:51][C:52]([C:56]([OH:84])([C:60]3[N:61]=[CH:62][N:63](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[CH:64]=3)[CH:57]([CH3:59])[CH3:58])=[CH:53][CH:54]=2)[CH:49]=[CH:48][C:47]=1[C:85](O)=[O:86].[NH4+].ON1C2C=CC=CC=2N=N1>>[Cl:45][C:46]1[C:55]2[C:50](=[CH:51][C:52]([C:56]([OH:84])([C:60]3[N:61]=[CH:62][NH:63][CH:64]=3)[CH:57]([CH3:59])[CH3:58])=[CH:53][CH:54]=2)[CH:49]=[CH:48][C:47]=1[C:85]([NH2:17])=[O:86]

Participants

4

Reactant 3

HCID 187691161-chloro-6-(1-hydroxy-2-methyl-1-(1-trityl-1H-imidazol-4-yl)propyl)-2-naphthoic acidHCID 18769130methyl 1-chloro-6-(1-hydroxy-2-methyl-1-(1-trityl-1H-imidazol-4-yl)propyl)-2-naphthoateHCID 220338091-Hydroxybenzotriazole, ammonium salt

Product 1

HCID 1784500771-Chloro-6-[1-hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl)-2-naphthamide

Procedure

In a manner to that described in Example 9-(i), methyl 1-chloro-6-(1-hydroxy-2-methyl-1-(1-trityl-1H-imidazol-4-yl)propyl)-2-naphthoate (2.83 g) was converted to 1-chloro-6-(1-hydroxy-2-methyl-1-(1-trityl-1H-imidazol-4-yl)propyl)-2-naphthoic acid, which was reacted with 1-hydroxybenzotriazole ammonium salt (533 mg) in a similar manner as described in Example 24-(i) to give the titled compound (904 mg) as a colorless powder.

Sources & evidence

ORD record
ord-f69ac988447d4f428d201850576b24aa
Source dataset
uspto-grants-2003_11
Patent number
US06649643B1

Reaction notes

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