3-Ethynyloxolan-3-ol → (+/-)-9-(3,4-Dihydroxy-3-methyl-but-1-ynyl)-8-fluoro-4,5-dihydro-6-oxa-3-thia-1-aza-benzo azulene-2-carboxylic acid amide

HRID 575241Notes

Reaction equation

HRID 575241 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.[C:20]([C:22]1([OH:27])[CH2:26]C[O:24][CH2:23]1)#[CH:21]>>[OH:27][C:22]([CH3:26])([CH2:23][OH:24])[C:20]#[C:21][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

Participants

3

Reactant 2

HCID 156999173-Ethynyloxolan-3-olHCID 866930599-Bromo-8-fluoro-4,5-dihydro-[1]benzoxepino[5,4-d]thiazole-2-carboxamide

Product 1

HCID 86693117(+/-)-9-(3,4-Dihydroxy-3-methyl-but-1-ynyl)-8-fluoro-4,5-dihydro-6-oxa-3-thia-1-aza-benzo azulene-2-carboxylic acid amideYield 14%

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 2-methylbut-3-yne-1,2-diol (US2010/144757 A1) to give the titled compound as a brown solid (30 mg, 14%).

Sources & evidence

ORD record
ord-f5f4d8de1ecb4bec9ddb48fe361e887b
Source dataset
uspto-grants-2015_05
Patent number
US09034866B2

Reaction notes

Loading…