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

HRID 575263Notes

Reaction equation

HRID 575263 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][O:19][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=4)=[C:13]([C:15]([NH2:17])=[O:16])[N:14]=[C:7]3[C:6]=2[CH:26]=1.BrC1C=CC2OCCN3C(CN4C=CN=C4C)=C(C(N)=O)N=C3C=2C=1.N1C=CC=CC1=O.[CH3:59][C:60]([OH:64])([C:62]#[CH:63])[CH3:61]>>[OH:64][C:60]([CH3:61])([CH3:59])[C:62]#[C:63][C:2]1[CH:3]=[CH:4][C:5]2[O:11][CH2:10][CH2:9][N:8]3[C:12]([CH2:18][O:19][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=4)=[C:13]([C:15]([NH2:17])=[O:16])[N:14]=[C:7]3[C:6]=2[CH:26]=1

Participants

5

Reactant 4

HCID 82582-Methyl-3-butyn-2-olHCID 88712-PyridoneHCID 8669327210-bromo-3((2-methyl-1H-imidazol-1-yl)methyl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamideHCID 8669328410-Bromo-3-((pyridin-2-yloxy)methyl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamide

Product 1

HCID 8669328310-(3-Hydroxy-3-methylbut-1-yn-1-yl)-3-((pyridin-2-yloxy)methyl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamideYield 5%

Procedure

Similar to as described in General Procedure G, 10-bromo-3-((pyridin-2-yloxy)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-pyridone) was reacted with 2-methylbut-3-yn-2-ol to give the titled compound as an off-white solid (5 mg, 5%).

Workup

  1. customprepared similarly

Sources & evidence

ORD record
ord-0cbcfcadf5af4e46bb9792024fa7a794
Source dataset
uspto-grants-2015_05
Patent number
US09034866B2

Reaction notes

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