2-Methyl-3-butyn-2-ol → 10-(3-Hydroxy-3-methylbut-1-yn-1-yl)-3-((2-oxopyrrolidin-1-yl)methyl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamide

HRID 575260Notes

Reaction equation

HRID 575260 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[O:11][CH2:10][CH2:9][N:8]3[C:12]([CH2:18][N:19]4[CH2:23][CH2:22][CH2:21][C:20]4=[O:24])=[C:13]([C:15]([NH2:17])=[O:16])[N:14]=[C:7]3[C:6]=2[CH:25]=1.BrC1C=CC2OCCN3C(CN4C=CN=C4C)=C(C(N)=O)N=C3C=2C=1.N1CCCC1=O.[CH3:57][C:58]([OH:62])([C:60]#[CH:61])[CH3:59]>>[OH:62][C:58]([CH3:59])([CH3:57])[C:60]#[C:61][C:2]1[CH:3]=[CH:4][C:5]2[O:11][CH2:10][CH2:9][N:8]3[C:12]([CH2:18][N:19]4[CH2:23][CH2:22][CH2:21][C:20]4=[O:24])=[C:13]([C:15]([NH2:17])=[O:16])[N:14]=[C:7]3[C:6]=2[CH:25]=1

Participants

5

Reactant 4

HCID 82582-Methyl-3-butyn-2-olHCID 120252-PyrrolidoneHCID 8669327210-bromo-3((2-methyl-1H-imidazol-1-yl)methyl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamideHCID 8669327610-Bromo-3-((2-oxopyrrolidin-1-yl)methyl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamide

Product 1

HCID 8669327510-(3-Hydroxy-3-methylbut-1-yn-1-yl)-3-((2-oxopyrrolidin-1-yl)methyl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamideYield 63%

Procedure

Similar to as described in General Procedure G, 10-bromo-3-((2-oxopyrrolidin-1-yl)methyl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamide (prepared similarly as described in the synthesis of 10-bromo-3-((2-methyl-1H-imidazol-1-yl)methyl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamide replacing 2-methylimidazole with 2-pyrrolidinone) was reacted with 2-methylbut-3-yn-2-ol to give the titled compound as a colorless solid (64 mg, 63%).

Workup

  1. customprepared similarly

Sources & evidence

ORD record
ord-54cdbd27a29147488fc8efed023604b0
Source dataset
uspto-grants-2015_05
Patent number
US09034866B2

Reaction notes

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