2-(4-Methylpyridin-2-yl)but-3-yn-2-ol → (+/-)-9-Fluoro-10-(3-hydroxy-3-(4-methylpyridin-2-yl)but-1-yn-1-yl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamide

HRID 575198Notes

Reaction equation

HRID 575198 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.[CH3:20][C:21]1[CH:26]=[CH:25][N:24]=[C:23]([C:27]([OH:31])([C:29]#[CH:30])[CH3:28])[CH:22]=1>>[F:19][C:3]1[C:2]([C:30]#[C:29][C:27]([OH:31])([C:23]2[CH:22]=[C:21]([CH3:20])[CH:26]=[CH:25][N:24]=2)[CH3:28])=[CH:18][C:6]2[C:7]3[N:8]([CH:12]=[C:13]([C:15]([NH2:17])=[O:16])[N:14]=3)[CH2:9][CH2:10][O:11][C:5]=2[CH:4]=1

Participants

3

Reactant 2

HCID 582216482-(4-Methylpyridin-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 86693207(+/-)-9-Fluoro-10-(3-hydroxy-3-(4-methylpyridin-2-yl)but-1-yn-1-yl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamideYield 10%

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-(4-methylpyridin-2-yl)but-3-yn-2-ol (WO2009/158011A1) to give the titled compound as a white solid (39 mg, 10%).

Sources & evidence

ORD record
ord-9c807025008e4042ab3ec5bc22d9a039
Source dataset
uspto-grants-2015_05
Patent number
US09034866B2

Reaction notes

Loading…