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

HRID 575259Notes

Reaction equation

HRID 575259 reaction equation
[N:1]1([CH2:6][C:7]2[N:11]3[CH2:12][CH2:13][O:14][C:15]4[CH:20]=[CH:19][C:18](Br)=[CH:17][C:16]=4[C:10]3=[N:9][C:8]=2[C:22]([NH2:24])=[O:23])[CH:5]=[CH:4][CH:3]=[N:2]1.BrC1C=CC2OCCN3C(CN4C=CN=C4C)=C(C(N)=O)N=C3C=2C=1.N1C=CC=N1.[CH3:55][C:56]([OH:60])([C:58]#[CH:59])[CH3:57]>>[N:1]1([CH2:6][C:7]2[N:11]3[CH2:12][CH2:13][O:14][C:15]4[CH:20]=[CH:19][C:18]([C:59]#[C:58][C:56]([OH:60])([CH3:57])[CH3:55])=[CH:17][C:16]=4[C:10]3=[N:9][C:8]=2[C:22]([NH2:24])=[O:23])[CH:5]=[CH:4][CH:3]=[N:2]1

Participants

5

Reactant 4

HCID 1048PyrazoleHCID 82582-Methyl-3-butyn-2-olHCID 8669327210-bromo-3((2-methyl-1H-imidazol-1-yl)methyl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamideHCID 866932743((1H-pyrazol-1-yl)methyl)-10-bromo-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamide

Product 1

HCID 866932733-((1H-pyrazol-1-yl)methyl)-10-(3-hydroxy-3-methylbut-1-yn-1-yl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamideYield 14%

Procedure

Similar to as described in General Procedure G, 3((1H-pyrazol-1-yl)methyl)-10-bromo-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 pyrazole) was reacted with 2-methylbut-3-yn-2-ol to give the titled compound as a colorless solid (14 mg, 14%).

Workup

  1. customprepared similarly

Sources & evidence

ORD record
ord-a4742eb8bc74429ca85c1a10b820e205
Source dataset
uspto-grants-2015_05
Patent number
US09034866B2

Reaction notes

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