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

HRID 575265Notes

Reaction equation

HRID 575265 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[C:23]5[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=5[N:21]=[C:20]4[CH3:28])=[C:13]([C:15]([NH2:17])=[O:16])[N:14]=[C:7]3[C:6]=2[CH:29]=1.BrC1C=CC2OCCN3C(CN4C=CN=C4C)=C(C(N)=O)N=C3C=2C=1.CC1NC2C=CC=CC=2N=1.[CH3:65][C:66]([OH:70])([C:68]#[CH:69])[CH3:67]>>[OH:70][C:66]([CH3:67])([CH3:65])[C:68]#[C:69][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[C:23]5[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=5[N:21]=[C:20]4[CH3:28])=[C:13]([C:15]([NH2:17])=[O:16])[N:14]=[C:7]3[C:6]=2[CH:29]=1

Participants

5

Reactant 4

HCID 82582-Methyl-3-butyn-2-olHCID 119842-MethylbenzimidazoleHCID 8669327210-bromo-3((2-methyl-1H-imidazol-1-yl)methyl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamideHCID 8669328810-bromo-3((2-methyl-1H-benzo[d]imidazol-1-yl)methyl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamide

Product 1

HCID 8669328710-(3-hydroxy-3-methylbut-1-yn-1-yl)-3-((2-methyl-1H-benzo[d]imidazol-1-yl)methyl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamideYield 24%

Procedure

Similar to as described in General Procedure G, 10-bromo-3-((2-methyl-1H-benzo[d]imidazol-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-((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-methylbenzimidazole) was reacted with 2-methylbut-3-yn-2-ol to give the titled compound as a colorless solid (26 mg, 24%).

Workup

  1. customprepared similarly

Sources & evidence

ORD record
ord-c95142bc23854a1da83ca8bc2e0c9d90
Source dataset
uspto-grants-2015_05
Patent number
US09034866B2

Reaction notes

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