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

HRID 575262Notes

Reaction equation

HRID 575262 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][C:21]=4[F:26])=[C:13]([C:15]([NH2:17])=[O:16])[N:14]=[C:7]3[C:6]=2[CH:27]=1.BrC1C=CC2OCCN3C(CN4C=CN=C4C)=C(C(N)=O)N=C3C=2C=1.FC1C=CC=CC=1O.[CH3:61][C:62]([OH:66])([C:64]#[CH:65])[CH3:63]>>[F:26][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=1[O:19][CH2:18][C:12]1[N:8]2[CH2:9][CH2:10][O:11][C:5]3[CH:4]=[CH:3][C:2]([C:65]#[C:64][C:62]([OH:66])([CH3:63])[CH3:61])=[CH:27][C:6]=3[C:7]2=[N:14][C:13]=1[C:15]([NH2:17])=[O:16]

Participants

5

Reactant 4

HCID 82582-Methyl-3-butyn-2-olHCID 97072-FluorophenolHCID 8669327210-bromo-3((2-methyl-1H-imidazol-1-yl)methyl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamideHCID 8669328210-Bromo-3((2-fluorophenoxy)methyl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamide

Product 1

HCID 866932813((2-Fluorophenoxy)methyl)-10-(3-hydroxy-3-methylbut-1-yn-1-yl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamideYield 6%

Procedure

Similar to as described in General Procedure G, 10-bromo-3((2-fluorophenoxy)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-fluorophenol) was reacted with 2-methylbut-3-yn-2-ol to give the titled compound as an off-white solid (7 mg, 6%).

Workup

  1. customprepared similarly

Sources & evidence

ORD record
ord-98cce18a6d89404f89f3deae515393e0
Source dataset
uspto-grants-2015_05
Patent number
US09034866B2

Reaction notes

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