3-[4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]pentan-1-ol → 6-((4'-(5-Hydroxypentyl)-(1,1'-biphenyl]-4-yl)sulfonyl)-4-((3-methoxyphenyl)amino)-8-methylquinoline-3-carboxamide

HRID 1944894Notes

Reaction equation

HRID 1944894 reaction equation
OC[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([S:15]([C:18]3[CH:19]=[C:20]4[C:25](=[C:26]([CH3:28])[CH:27]=3)[N:24]=[CH:23][C:22]([C:29]([NH2:31])=[O:30])=[C:21]4[NH:32][C:33]3[CH:38]=[CH:37][CH:36]=[C:35]([O:39][CH3:40])[CH:34]=3)(=[O:17])=[O:16])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.CC1(C)C(C)(C)OB(C2C=C[C:52]([CH:55](CC)[CH2:56][CH2:57][OH:58])=[CH:51]C=2)O1>>[OH:58][CH2:57][CH2:56][CH2:55][CH2:52][CH2:51][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:14]=[CH:13][C:12]([S:15]([C:18]3[CH:19]=[C:20]4[C:25](=[C:26]([CH3:28])[CH:27]=3)[N:24]=[CH:23][C:22]([C:29]([NH2:31])=[O:30])=[C:21]4[NH:32][C:33]3[CH:38]=[CH:37][CH:36]=[C:35]([O:39][CH3:40])[CH:34]=3)(=[O:17])=[O:16])=[CH:11][CH:10]=2)=[CH:7][CH:8]=1

Participants

3

Reactant 2

HCID 575169483-[4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]pentan-1-olHCID 66988803HCID 66988803, compound

Product 1

HCID 669889456-((4'-(5-Hydroxypentyl)-(1,1'-biphenyl]-4-yl)sulfonyl)-4-((3-methoxyphenyl)amino)-8-methylquinoline-3-carboxamide

Procedure

The title compound was synthesized in a manner analogous to that described for Intermediate 65, using 3-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]pentan-1-ol in place of 4-(hydroxymethyl)phenylboronic acid. ES/MS calcd. for C35H36N3O5S+ 610.2. Found m/z=610.3 (M+H)+.

Sources & evidence

ORD record
ord-d3871e7b39264da78153106179ea2993
Source dataset
uspto-grants-2013_03
Patent number
US08394829B2

Reaction notes

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