(3-Bromopropoxy)(tert-butyl)dimethylsilane → (S)-4-{[[2-Fluoro-3-(3-hydroxypropoxy)-5-methoxyphenyl]-(5-oxo-1-pyrimidin-2-yl-4,5-dihydro-1H-[1,2,4]triazol-3-yl)methyl]amino}benzamidine acetate

HRID 1161597Notes

Reaction equation

HRID 1161597 reaction equation
[C:1]([OH:4])(=[O:3])[CH3:2].[F:5][C:6]1[C:11]([O:12][CH2:13]CO)=[CH:10][C:9]([O:16][CH3:17])=[CH:8][C:7]=1[C@H:18]([NH:31][C:32]1[CH:40]=[CH:39][C:35]([C:36]([NH2:38])=[NH:37])=[CH:34][CH:33]=1)[C:19]1[NH:23][C:22](=[O:24])[N:21]([C:25]2[N:30]=[CH:29][CH:28]=[CH:27][N:26]=2)[N:20]=1.BrC[CH2:43][CH2:44][O:45][Si](C(C)(C)C)(C)C>>[C:1]([OH:4])(=[O:3])[CH3:2].[F:5][C:6]1[C:11]([O:12][CH2:13][CH2:43][CH2:44][OH:45])=[CH:10][C:9]([O:16][CH3:17])=[CH:8][C:7]=1[C@H:18]([NH:31][C:32]1[CH:33]=[CH:34][C:35]([C:36]([NH2:38])=[NH:37])=[CH:39][CH:40]=1)[C:19]1[NH:23][C:22](=[O:24])[N:21]([C:25]2[N:26]=[CH:27][CH:28]=[CH:29][N:30]=2)[N:20]=1

Participants

3

Reactant 2

HCID 607486(3-Bromopropoxy)(tert-butyl)dimethylsilaneHCID 136366370(S)-4-({[2-fluoro-3-(2-hydroxyethoxy)-5-methoxyphenyl]-(5-oxo-1-pyrimidin-2-yl-4,5-dihydro-1H-[1,2,4]triazol-3-yl)methyl}amino)benzamidine acetate

Product 1

HCID 136389300(S)-4-{[[2-Fluoro-3-(3-hydroxypropoxy)-5-methoxyphenyl]-(5-oxo-1-pyrimidin-2-yl-4,5-dihydro-1H-[1,2,4]triazol-3-yl)methyl]amino}benzamidine acetate

Procedure

The same procedure was carried out as in Examples (153a) to (153b), except that (3-bromopropoxy)-t-butyldimethylsilane was used instead of 2-(2-bromoethoxy)tetrahydro-2H-pyran in Example (153a), to give the first eluting enantiomer of the title compound.

Sources & evidence

ORD record
ord-0487a8da7fcc4721b212b3b4642e4e83
Source dataset
uspto-grants-2010_10
Patent number
US07816522B2

Reaction notes

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