Ammonia → (+/-)-9-(3-Carbamoyl-3-hydroxy-but-1-ynyl)-8-fluoro-4,5-dihydro-6-oxa-1,3a-diaza-benzo[e]azulene-2-carboxylic acid amide
Reaction equation
[C:1]([C:4]1[N:5]=[C:6]2[C:12]3[CH:13]=[C:14]([C:18]#[C:19][C:20]([OH:26])([CH3:25])[C:21](OC)=[O:22])[C:15]([F:17])=[CH:16][C:11]=3[O:10][CH2:9][CH2:8][N:7]2[CH:27]=1)(=[O:3])[NH2:2].OC(C)(C#C)C(OC)=O.BrC1C(F)=CC2OCC[N:44]3C=C(C(N)=O)N=C3C=2C=1.N>CO>[NH2:44][C:21](=[O:22])[C:20]([OH:26])([CH3:25])[C:19]#[C:18][C:14]1[C:15]([F:17])=[CH:16][C:11]2[O:10][CH2:9][CH2:8][N:7]3[CH:27]=[C:4]([C:1]([NH2:2])=[O:3])[N:5]=[C:6]3[C:12]=2[CH:13]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
similar to General Procedure M, A solution of methyl 4-(2-carbamoyl-9-fluoro-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepin-10-yl)-2-hydroxy-2-methylbut-3-ynoate (300 mg, 0.80 mmol, 1.00 equiv) (prepared by reaction of methyl 2-hydroxy-2-methylbut-3-ynoate and 10-bromo-9-fluoro-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamide in methanol saturated with ammonia (40 mL) was stirred for 12 h at 25° C. The resulting mixture was concentrated under vacuum. The residue was washed with 3×10 mL of methanol and 2×5 mL of CH3CN. The solid was dried in an oven under reduced pressure. This resulted in 43 mg (15%) of the title compound as a brown solid.
Workup
- concentrationThe resulting mixture was concentrated under vacuum
- washThe residue was washed with 3×10 mL of methanol and 2×5 mL of CH3CN
- customThe solid was dried in an oven under reduced pressure
Sources & evidence
- ORD record
- ord-8e18aea6610f417abed1d822fdf05173
- Source dataset
- uspto-grants-2015_05
- Patent number
- US09034866B2
Reaction notes
Loading…