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

HRID 575250Notes

Reaction equation

HRID 575250 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]([CH3:21])[CH3:20])=[C:13]([C:15]([NH2:17])=[O:16])[N:14]=[C:7]3[C:6]=2[CH:22]=1.BrC1C=CC2OCCN3C(CN4CCCC4)=C(C(N)=O)N=C3C=2C=1.CNC.[CH3:50][C:51]([OH:55])([C:53]#[CH:54])[CH3:52]>>[CH3:20][N:19]([CH2:18][C:12]1[N:8]2[CH2:9][CH2:10][O:11][C:5]3[CH:4]=[CH:3][C:2]([C:54]#[C:53][C:51]([OH:55])([CH3:52])[CH3:50])=[CH:22][C:6]=3[C:7]2=[N:14][C:13]=1[C:15]([NH2:17])=[O:16])[CH3:21]

Participants

5

Reactant 4

HCID 674DimethylamineHCID 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 8669325510-Bromo-3-((dimethylamino)methyl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamide

Product 1

HCID 866932543-((Dimethylamino)methyl)-10-(3-hydroxy-3-methylbut-1-yn-1-yl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamideYield 34%

Procedure

Similar to as described in General Procedure G, 10-bromo-3-((dimethylamino)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 dimethylamine) was reacted with 2-methylbut-3-yn-2-ol to give the titled compound as a grey solid (41 mg, 34%).

Workup

  1. customprepared similarly

Sources & evidence

ORD record
ord-70949910d1a44b6b88f7119e2d57ca8a
Source dataset
uspto-grants-2015_05
Patent number
US09034866B2

Reaction notes

Loading…