TBDMS ether → 10-(4-Hydroxy-3,3-dimethylbut-1-yn-1-yl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamide

HRID 575237Notes

Reaction equation

HRID 575237 reaction equation
Br[C:2]1[CH:3]=[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.C([Si]([O:26][CH2:27][C:28]([CH3:32])([CH3:31])[C:29]#[CH:30])(C)C)(C)(C)C.[Si](O[Si](C(C)(C)C)(C)C)(C(C)(C)C)(C)C>CC#N>[OH:26][CH2:27][C:28]([CH3:32])([CH3:31])[C:29]#[C:30][C:2]1[CH:3]=[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

5

Reactant 3

HCID 590018TBDMS etherHCID 6831288310-Bromo-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamideHCID 86669580Tert-butyl-(2,2-dimethyl-but-3-ynyloxy)-dimethyl-silane

Product 1

HCID 7171545410-(4-Hydroxy-3,3-dimethylbut-1-yn-1-yl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamideYield 28%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Similar to as described in General Procedure G, 10-bromo-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamide was reacted with tert-butyl[(2,2-dimethylbut-3-yn-1-yl)oxy]dimethylsilane to give the titled compound as a off-white solid (35 mg, 28%) after deprotection of the tert-butyldimethylsilyl ether (HF/MeCN).

Sources & evidence

ORD record
ord-2cb8ae7c346648a6b6fef9a920bc995f
Source dataset
uspto-grants-2015_05
Patent number
US09034866B2

Reaction notes

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