9-Bromo-8-fluoro-4,5-dihydro-[1]benzoxepino[5,4-d]thiazole-2-carboxamide → (+/-)-8-Fluoro-9-(4-fluoro-3-hydroxy-3-methyl-but-1-ynyl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene-2-carboxylic acid amide

HRID 575246Notes

Reaction equation

HRID 575246 reaction equation
Br[C:2]1[C:18]([F:19])=[CH:17][C:5]2[O:6][CH2:7][CH2:8][C:9]3[S:13][C:12]([C:14]([NH2:16])=[O:15])=[N:11][C:10]=3[C:4]=2[CH:3]=1.[F:20][CH2:21][C:22]([CH3:26])([OH:25])[C:23]#[CH:24]>>[F:19][C:18]1[C:2]([C:24]#[C:23][C:22]([OH:25])([CH3:26])[CH2:21][F:20])=[CH:3][C:4]2[C:10]3[N:11]=[C:12]([C:14]([NH2:16])=[O:15])[S:13][C:9]=3[CH2:8][CH2:7][O:6][C:5]=2[CH:17]=1

Participants

3

Reactant 2

HCID 866930599-Bromo-8-fluoro-4,5-dihydro-[1]benzoxepino[5,4-d]thiazole-2-carboxamideHCID 866931131-Fluoro-2-methylbut-3-yn-2-ol

Product 1

HCID 71715339(+/-)-8-Fluoro-9-(4-fluoro-3-hydroxy-3-methyl-but-1-ynyl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene-2-carboxylic acid amideYield 28%

Procedure

Similar to as described in General Procedure G, 9-bromo-8-fluoro-4,5-dihydrobenzo[2,3]oxepino[4,5-d]thiazole-2-carboxamide was reacted with 1-fluoro-2-methylbut-3-yn-2-ol to give the titled compound as an off-white solid (6 mg, 28%).

Sources & evidence

ORD record
ord-7a85a1785e6b4d978883a57ad38e6f6d
Source dataset
uspto-grants-2015_05
Patent number
US09034866B2

Reaction notes

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