2-Methylbut-3-yne-1,2-diol → (+/-)-10-(3,4-Dihydroxy-3-methylbut-1-yn-1-yl)-9-fluoro-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamide

HRID 575209Notes

Reaction equation

HRID 575209 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]([OH:26])([C:24]#[CH:25])[CH2:22][OH:23]>>[OH:26][C:21]([CH3:20])([CH2:22][OH:23])[C:24]#[C:25][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

Participants

3

Reactant 2

HCID 221369052-Methylbut-3-yne-1,2-diolHCID 8669305110-Bromo-9-fluoro-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamide

Product 1

HCID 71715108(+/-)-10-(3,4-Dihydroxy-3-methylbut-1-yn-1-yl)-9-fluoro-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamideYield 15%

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-methylbut-3-yne-1,2-diol to give the titled compound as an off-white solid (30.8 mg, 15%).

Sources & evidence

ORD record
ord-ff138e056b2740b4ac36eac54c674274
Source dataset
uspto-grants-2015_05
Patent number
US09034866B2

Reaction notes

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