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

HRID 575255Notes

Reaction equation

HRID 575255 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][CH2:20][CH2:21][O:22][CH3:23])=[C:13]([C:15]([NH2:17])=[O:16])[N:14]=[C:7]3[C:6]=2[CH:24]=1.BrC1C=CC2OCCN3C(CN4CCCC4)=C(C(N)=O)N=C3C=2C=1.COCCN.[CH3:54][C:55]([OH:59])([C:57]#[CH:58])[CH3:56]>>[OH:59][C:55]([CH3:56])([CH3:54])[C:57]#[C:58][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][CH2:20][CH2:21][O:22][CH3:23])=[C:13]([C:15]([NH2:17])=[O:16])[N:14]=[C:7]3[C:6]=2[CH:24]=1

Participants

5

Reactant 4

HCID 80182-MethoxyethylamineHCID 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 8669326510-Bromo-3-(((2-methoxyethyl)amino)methyl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamide

Product 1

HCID 8669326410-(3-Hydroxy-3-methylbut-1-yn-1-yl)-3-(((2-methoxyethyl)amino)methyl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamideYield 20%

Procedure

Similar to as described in General Procedure G, 10-bromo-3-(((2-methoxyethyl)amino)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 2-methoxyethanamine) was reacted with 2-methylbut-3-yn-2-ol to give the titled compound as a colorless solid (25 mg, 20%).

Workup

  1. customprepared similarly

Sources & evidence

ORD record
ord-84906ec79cce4e56ab3d1cf9b5fcadb1
Source dataset
uspto-grants-2015_05
Patent number
US09034866B2

Reaction notes

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