2-(5-Chloropyridin-2-yl)but-3-yn-2-ol → (+/-)-10-(3-(5-Chloropyridin-2-yl)-3-hydroxybut-1-yn-1-yl)-9-fluoro-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamide

HRID 575219Notes

Reaction equation

HRID 575219 reaction equation
Br[C:2]1[C:3]([F:19])=[CH:4][C:5]2[O:11][CH2:10][CH2:9][N:8]3[CH:12]=[C:13]([C:15]([NH2:17])=[O:16])[N:14]=[C:7]3[C:6]=2[CH:18]=1.[Cl:20][C:21]1[CH:22]=[CH:23][C:24]([C:27]([OH:31])([C:29]#[CH:30])[CH3:28])=[N:25][CH:26]=1>>[Cl:20][C:21]1[CH:22]=[CH:23][C:24]([C:27]([OH:31])([CH3:28])[C:29]#[C:30][C:2]2[C:3]([F:19])=[CH:4][C:5]3[O:11][CH2:10][CH2:9][N:8]4[CH:12]=[C:13]([C:15]([NH2:17])=[O:16])[N:14]=[C:7]4[C:6]=3[CH:18]=2)=[N:25][CH:26]=1

Participants

3

Reactant 2

HCID 866696112-(5-Chloropyridin-2-yl)but-3-yn-2-olHCID 8669305110-Bromo-9-fluoro-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamide

Product 1

HCID 71715336(+/-)-10-(3-(5-Chloropyridin-2-yl)-3-hydroxybut-1-yn-1-yl)-9-fluoro-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamideYield 28%

Procedure

Similar to as described in General Procedure G, 10-bromo-9-fluoro-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamide was reacted with 2-(5-chloropyridin-2-yl)but-3-yn-2-ol to give the titled compound as a grey solid (60 mg, 28%).

Sources & evidence

ORD record
ord-efd392e9e1ad4fec8a2dacb584665f82
Source dataset
uspto-grants-2015_05
Patent number
US09034866B2

Reaction notes

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