2-Methyl-3-butyn-2-ol → (+/-)-9-Fluoro-3-(hydroxy(4-methylthiazol-5-yl)methyl)-10-(3-hydroxy-3-methylbut-1-yn-1-yl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamide

HRID 575392Notes

Reaction equation

HRID 575392 reaction equation
Br[C:2]1[C:3]([F:27])=[CH:4][C:5]2[O:11][CH2:10][CH2:9][N:8]3[C:12]([CH:18]([OH:25])[C:19]4[S:23][CH:22]=[N:21][C:20]=4[CH3:24])=[C:13]([C:15]([NH2:17])=[O:16])[N:14]=[C:7]3[C:6]=2[CH:26]=1.[CH3:28][C:29]([OH:33])([CH3:32])[C:30]#[CH:31]>>[F:27][C:3]1[C:2]([C:31]#[C:30][C:29]([OH:33])([CH3:32])[CH3:28])=[CH:26][C:6]2[C:7]3[N:8]([C:12]([CH:18]([OH:25])[C:19]4[S:23][CH:22]=[N:21][C:20]=4[CH3:24])=[C:13]([C:15]([NH2:17])=[O:16])[N:14]=3)[CH2:9][CH2:10][O:11][C:5]=2[CH:4]=1

Participants

3

Reactant 2

HCID 82582-Methyl-3-butyn-2-olHCID 8669343910-Bromo-9-fluoro-3-[hydroxy-(4-methylthiazol-5-yl)methyl]-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine-2-carboxamide

Product 1

HCID 86693440(+/-)-9-Fluoro-3-(hydroxy(4-methylthiazol-5-yl)methyl)-10-(3-hydroxy-3-methylbut-1-yn-1-yl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamideYield 18%

Procedure

9-fluoro-3-(hydroxy(4-methylthiazol-5-yl)methyl)-10-(3-hydroxy-3-methylbut-1-yn-1-yl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamide was prepared similarly according to General Procedure G with slight modifications. 10-bromo-9-fluoro-3-[hydroxy-(4-methylthiazol-5-yl)methyl]-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine-2-carboxamide was reacted with 3-methyl-1-butyne-3-ol to afford 5.4 mg of the titled compound (18% yield). M+1=457.1. 1H NMR (400 MHz, DMSO) δ 8.87 (s, 1H), 8.58 (d, J=8.3 Hz, 1H), 8.01 (br s, 1H), 7.59-7.53 (m, 2H), 7.00 (d, J=10.5 Hz, 1H), 6.94 (d, J=6.3 Hz, 1H), 5.54 (s, 1H), 4.57-4.48 (m, 1H), 4.48-4.36 (m, 2H), 4.31-4.22 (m, 1H), 2.25 (s, 3H), 1.49 (s, 6H).

Workup

  1. custom9-fluoro-3-(hydroxy(4-methylthiazol-5-yl)methyl)-10-(3-hydroxy-3-methylbut-1-yn-1-yl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamide was prepared similarly

Sources & evidence

ORD record
ord-b63b04cd9c3f413184df1797615dd284
Source dataset
uspto-grants-2015_05
Patent number
US09034866B2

Reaction notes

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