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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 575472Generated: October 30, 2026

1-Methoxy-2-methylbut-3-yn-2-ol → (+/-)-3-cyclopropyl-9-fluoro-10-(3-hydroxy-4-methoxy-3-methylbut-1-yn-1-yl)-6,7-dihydro-5H-5,7-methanobenzo[c]imidazo[1,2-a]azepine-2-carboxamide

https://huagongshe.com/reaction/575472

Reaction equation

Participants

RoleNameHCIDCharge
Reactant1-Methoxy-2-methylbut-3-yn-2-olHCID 21706426—
Reactant10-bromo-3-cyclopropyl-9-fluoro-6,7-dihydro-5H-5,7-methanobenzo[c]imidazo[1,2-a]azepine-2-carboxamideHCID 86693537—
Product(+/-)-3-cyclopropyl-9-fluoro-10-(3-hydroxy-4-methoxy-3-methylbut-1-yn-1-yl)-6,7-dihydro-5H-5,7-methanobenzo[c]imidazo[1,2-a]azepine-2-carboxamideHCID 86693539—

Reaction Steps

Similar to as described in General Procedure G, 10-bromo-3-cyclopropyl-9-fluoro-6,7-dihydro-5H-5,7-methanobenzo[c]imidazo[1,2-a]azepine-2-carboxamide was reacted with 1-methoxy-2-methylbut-3-yn-2-ol to give the titled compound. MS+410.2. 1H NMR (400 MHz, DMSO) δ 8.66 (d, J=7.5 Hz, 1H), 7.47 (br s, 1H), 7.25 (d, J=10.1 Hz, 1H), 6.98 (br s, 1H), 5.68 (s, 1H), 5.26 (m, 1H), 3.68 (m, 1H), 3.39 (m, 2H), 3.37 (s, 3H), 3.14 (m, 2H), 1.81-1.59 (overlapping m, 3H), 1.45 (s, 3H), 0.99 (m, 2H), 0.67 (m, 2H).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09034866B2
Source datasetuspto-grants-2015_05
ORD IDord-428a1b6fc0184cd083dfa6c20f139782
Source noteuspto-grants-2015_05