2-(Pyridin-2-yl)but-3-yn-2-ol → (+/-)-3-Cyclopropyl-9-fluoro-10-[3-hydroxy-3-(2-pyridyl)but-1-ynyl]-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine-2-carboxamide

HRID 575308Notes

Reaction equation

HRID 575308 reaction equation
Br[C:2]1[C:3]([F:22])=[CH:4][C:5]2[O:11][CH2:10][CH2:9][N:8]3[C:12]([CH:18]4[CH2:20][CH2:19]4)=[C:13]([C:15]([NH2:17])=[O:16])[N:14]=[C:7]3[C:6]=2[CH:21]=1.[N:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[C:29]([OH:33])([C:31]#[CH:32])[CH3:30]>>[CH:18]1([C:12]2[N:8]3[CH2:9][CH2:10][O:11][C:5]4[CH:4]=[C:3]([F:22])[C:2]([C:32]#[C:31][C:29]([OH:33])([C:24]5[CH:25]=[CH:26][CH:27]=[CH:28][N:23]=5)[CH3:30])=[CH:21][C:6]=4[C:7]3=[N:14][C:13]=2[C:15]([NH2:17])=[O:16])[CH2:20][CH2:19]1

Participants

3

Reactant 2

HCID 167625022-(Pyridin-2-yl)but-3-yn-2-olHCID 8669316910-Bromo-3-cyclopropyl-9-fluoro-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine-2-carboxamide

Product 1

HCID 86693340(+/-)-3-Cyclopropyl-9-fluoro-10-[3-hydroxy-3-(2-pyridyl)but-1-ynyl]-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine-2-carboxamideYield 16%

Procedure

10-bromo-3-cyclopropyl-9-fluoro-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamide was reacted with 2-(pyridin-2-yl)but-3-yn-2-ol via General Procedure E to yield 9.5 mg (16%) of (±)-3-cyclopropyl-9-fluoro-10-[3-hydroxy-3-(2-pyridyl)but-1-ynyl]-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine-2-carboxamide.

Sources & evidence

ORD record
ord-5e5a564150de450b990a67ea1127c7e6
Source dataset
uspto-grants-2015_05
Patent number
US09034866B2

Reaction notes

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