(R)-2-(pyridin-2-yl)but-3-yn-2-ol → (R)-9-fluoro-10-(3-hydroxy-3-(pyridin-2-yl)but-1-yn-1-yl)-6,7-dihydro-5H-5,7-methanobenzo[c]imidazo[1,2-a]azepine-2-carboxamide

HRID 575478Notes

Reaction equation

HRID 575478 reaction equation
Br[C:2]1[C:3]([F:20])=[CH:4][C:5]2[CH:11]3[CH2:12][CH:9]([CH2:10]3)[N:8]3[CH:13]=[C:14]([C:16]([NH2:18])=[O:17])[N:15]=[C:7]3[C:6]=2[CH:19]=1.[N:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[C@:27]([OH:31])([C:29]#[CH:30])[CH3:28]>>[F:20][C:3]1[C:2]([C:30]#[C:29][C@@:27]([OH:31])([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][N:21]=2)[CH3:28])=[CH:19][C:6]2[C:7]3[N:8]([CH:13]=[C:14]([C:16]([NH2:18])=[O:17])[N:15]=3)[CH:9]3[CH2:12][CH:11]([C:5]=2[CH:4]=1)[CH2:10]3

Participants

3

Reactant 2

HCID 42554703(R)-2-(pyridin-2-yl)but-3-yn-2-olHCID 8669308010-bromo-9-fluoro-6,7-dihydro-5H-5,7-methanobenzo[c]imidazo[1,2-a]azepine-2-carboxamide

Product 1

HCID 86693548(R)-9-fluoro-10-(3-hydroxy-3-(pyridin-2-yl)but-1-yn-1-yl)-6,7-dihydro-5H-5,7-methanobenzo[c]imidazo[1,2-a]azepine-2-carboxamide

Procedure

Similar to as described in General Procedure F, reaction of 10-bromo-9-fluoro-6,7-dihydro-5H-5,7-methanobenzo[c]imidazo[1,2-a]azepine-2-carboxamide with (R)-2-(pyridin-2-yl)but-3-yn-2-ol gave the titled compound.

Sources & evidence

ORD record
ord-6ab927f4731a4ff09b4acbb94344a412
Source dataset
uspto-grants-2015_05
Patent number
US09034866B2

Reaction notes

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