(S)-tert-Butyl 4-(1-cyano-2-(4-(4-methyl-3-oxo-3,4-dihydro-2H-benzo[b][1,4]thiazin-7-yl)phenyl)ethylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate → (S)-4-Amino-N-(1-cyano-2-(4-(4-methyl-3-oxo-3,4-dihydro-2H-benzo[b][1,4]thiazin-7-yl)phenyl)ethyl)tetrahydro-2H-pyran-4-carboxamide
Reaction equation
[C:1]([C@@H:3]([NH:23][C:24]([C:26]1([NH:32]C(=O)OC(C)(C)C)[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1)=[O:25])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:12]=[CH:13][C:14]3[N:19]([CH3:20])[C:18](=[O:21])[CH2:17][S:16][C:15]=3[CH:22]=2)=[CH:7][CH:6]=1)#[N:2]>C(O)=O>[NH2:32][C:26]1([C:24]([NH:23][C@H:3]([C:1]#[N:2])[CH2:4][C:5]2[CH:6]=[CH:7][C:8]([C:11]3[CH:12]=[CH:13][C:14]4[N:19]([CH3:20])[C:18](=[O:21])[CH2:17][S:16][C:15]=4[CH:22]=3)=[CH:9][CH:10]=2)=[O:25])[CH2:27][CH2:28][O:29][CH2:30][CH2:31]1Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
(S)-tert-Butyl 4-(1-cyano-2-(4-(4-methyl-3-oxo-3,4-dihydro-2H-benzo[b][1,4]thiazin-7-yl)phenyl)ethylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate (Example 28, step (iii), 120 mg) in formic acid (2 mL) was heated at 50° C. for 20 mins. The solvent was removed under reduced pressure and the residue azeotroped with methanol. The product was purified by reversed phase HPLC using methanol in 0.1% aqueous TFA and then converted to the free base by elution through a PL-HCO3 MP cartridge with dichloromethane/methanol to afford the titled compound (51 mg).