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

HRID 575253Notes

Reaction equation

HRID 575253 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][C@@H:21]([OH:24])[CH2:20]4)=[C:13]([C:15]([NH2:17])=[O:16])[N:14]=[C:7]3[C:6]=2[CH:25]=1.BrC1C=CC2OCCN3C(CN4CCCC4)=C(C(N)=O)N=C3C=2C=1.O[C@@H]1CCNC1.[CH3:56][C:57]([OH:61])([C:59]#[CH:60])[CH3:58]>>[OH:61][C:57]([CH3:58])([CH3:56])[C:59]#[C:60][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][C@@H:21]([OH:24])[CH2:20]4)=[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 2759337(R)-3-PyrrolidinolHCID 8669325310-Bromo-3-(pyrrolidin-1-ylmethyl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamideHCID 86693261(R)-10-bromo-3((3-hydroxypyrrolidin-1-yl)methyl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamide

Product 1

HCID 86693260(R)-10-(3-hydroxy-3-methylbut-1-yn-1-yl)-3-((3-hydroxypyrrolidin-1-yl)methyl)-5,6-dihydrobenzo [f]imidazo[1,2-d][1,4]oxazepine-2-carboxamideYield 14%

Procedure

Similar to as described in General Procedure G, (R)-10-bromo-3((3-hydroxypyrrolidin-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-(pyrrolidin-1-ylmethyl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamide replacing pyrrolidine with (R)-3-hydroxypyrrolidine) was reacted with 2-methylbut-3-yn-2-ol to give the titled compound as a white solid (11 mg, 14%).

Workup

  1. customprepared similarly

Sources & evidence

ORD record
ord-656e10c44c784f9b8c31e8db585b898d
Source dataset
uspto-grants-2015_05
Patent number
US09034866B2

Reaction notes

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