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

HRID 575252Notes

Reaction equation

HRID 575252 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][NH:19][CH:20]([CH3:22])[CH3:21])=[C:13]([C:15]([NH2:17])=[O:16])[N:14]=[C:7]3[C:6]=2[CH:23]=1.BrC1C=CC2OCCN3C(CN4CCCC4)=C(C(N)=O)N=C3C=2C=1.C(N)(C)C.[CH3:52][C:53]([OH:57])([C:55]#[CH:56])[CH3:54]>>[OH:57][C:53]([CH3:54])([CH3:52])[C:55]#[C:56][C:2]1[CH:3]=[CH:4][C:5]2[O:11][CH2:10][CH2:9][N:8]3[C:12]([CH2:18][NH:19][CH:20]([CH3:22])[CH3:21])=[C:13]([C:15]([NH2:17])=[O:16])[N:14]=[C:7]3[C:6]=2[CH:23]=1

Participants

5

Reactant 4

HCID 6363IsopropylamineHCID 82582-Methyl-3-butyn-2-olHCID 8669325310-Bromo-3-(pyrrolidin-1-ylmethyl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamideHCID 8669325910-Bromo-3-((isopropylamino)methyl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamide

Product 1

HCID 8669325810-(3-Hydroxy-3-methylbut-1-yn-1-yl)-3-((isopropylamino)methyl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamideYield 39%

Procedure

Similar to as described in General Procedure G, 10-bromo-3-((isopropylamino)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-(pyrrolidin-1-ylmethyl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamide replacing pyrrolidine with isopropylamine) was reacted with 2-methylbut-3-yn-2-ol to give the titled compound as a brown solid (16 mg, 39%).

Workup

  1. customprepared similarly

Sources & evidence

ORD record
ord-c0105f65791c4e70828a1b335a76edc1
Source dataset
uspto-grants-2015_05
Patent number
US09034866B2

Reaction notes

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