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

HRID 575199Notes

Reaction equation

HRID 575199 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[C:22]([C:27]([OH:31])([C:29]#[CH:30])[CH3:28])=[N:23][CH:24]=[CH:25][CH:26]=1>>[F:19][C:3]1[C:2]([C:30]#[C:29][C:27]([OH:31])([C:22]2[C:21]([CH3:20])=[CH:26][CH:25]=[CH:24][N:23]=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 8669305110-Bromo-9-fluoro-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamideHCID 866930912-(3-Methylpyridin-2-yl)but-3-yn-2-ol

Product 1

HCID 717151659-Fluoro-10-(3-hydroxy-3-(3-methylpyridin-2-yl)but-1-yn-1-yl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamideYield 7%

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-(3-methylpyridin-2-yl)but-3-yn-2-ol to give the titled compound as a yellow solid (15.0 mg, 7%).

Sources & evidence

ORD record
ord-4d2f5f1aaca84255a36afa4c165c05cf
Source dataset
uspto-grants-2015_05
Patent number
US09034866B2

Reaction notes

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