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

HRID 575472Notes

Reaction equation

HRID 575472 reaction equation
Br[C:2]1[C:3]([F:23])=[CH:4][C:5]2[CH:11]3[CH2:12][CH:9]([CH2:10]3)[N:8]3[C:13]([CH:19]4[CH2:21][CH2:20]4)=[C:14]([C:16]([NH2:18])=[O:17])[N:15]=[C:7]3[C:6]=2[CH:22]=1.[CH3:24][O:25][CH2:26][C:27]([CH3:31])([OH:30])[C:28]#[CH:29]>>[CH:19]1([C:13]2[N:8]3[CH:9]4[CH2:10][CH:11]([C:5]5[CH:4]=[C:3]([F:23])[C:2]([C:29]#[C:28][C:27]([OH:30])([CH3:31])[CH2:26][O:25][CH3:24])=[CH:22][C:6]=5[C:7]3=[N:15][C:14]=2[C:16]([NH2:18])=[O:17])[CH2:12]4)[CH2:20][CH2:21]1

Participants

3

Reactant 2

HCID 217064261-Methoxy-2-methylbut-3-yn-2-olHCID 8669353710-bromo-3-cyclopropyl-9-fluoro-6,7-dihydro-5H-5,7-methanobenzo[c]imidazo[1,2-a]azepine-2-carboxamide

Product 1

HCID 86693539(+/-)-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

Procedure

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).

Sources & evidence

ORD record
ord-428a1b6fc0184cd083dfa6c20f139782
Source dataset
uspto-grants-2015_05
Patent number
US09034866B2

Reaction notes

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