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

HRID 575213Notes

Reaction equation

HRID 575213 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:24]([OH:28])([C:26]#[CH:27])[CH3:25])[CH2:23][CH2:22]1>>[F:19][C:3]1[C:2]([C:27]#[C:26][C:24]([OH:28])([C:21]2([CH3:20])[CH2:23][CH2:22]2)[CH3:25])=[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 5232122-(1-Methylcyclopropyl)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 71715166(+/-)-9-Fluoro-10-(3-hydroxy-3-(1-methylcyclopropyl)but-1-yn-1-yl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamideYield 8%

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-(1-methylcyclopropyl)but-3-yn-2-ol to give the titled compound as a light brown solid (7.8 mg, 8%).

Sources & evidence

ORD record
ord-1db34c5904384af4a7c89b99d17de61b
Source dataset
uspto-grants-2015_05
Patent number
US09034866B2

Reaction notes

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