Hydrochloric Acid → 1-(7-(5-Amino-6-(5-(4-((methylamino)methyl)phenyl)-1,3,4-oxadiazol-2-yl)pyrazin-2-yl)-2,7-diazaspiro[4.4]nonan-2-yl)propan-1-one
Reaction equation
C(OC([N:8](C(OC(C)(C)C)=O)[C:9]1[C:10]([C:28]2[O:32][C:31]([C:33]3[CH:38]=[CH:37][C:36]([CH2:39][N:40](C)[C:41](=O)OC(C)(C)C)=[CH:35][CH:34]=3)=[N:30][N:29]=2)=[N:11][C:12]([N:15]2[CH2:27][CH2:26][C:17]3([CH2:21][CH2:20][N:19]([C:22](=[O:25])[CH2:23][CH3:24])[CH2:18]3)[CH2:16]2)=[CH:13][N:14]=1)=O)(C)(C)C.Cl>O1CCOCC1>[NH2:8][C:9]1[N:14]=[CH:13][C:12]([N:15]2[CH2:27][CH2:26][C:17]3([CH2:18][N:19]([C:22](=[O:25])[CH2:23][CH3:24])[CH2:20][CH2:21]3)[CH2:16]2)=[N:11][C:10]=1[C:28]1[O:32][C:31]([C:33]2[CH:38]=[CH:37][C:36]([CH2:39][NH:40][CH3:41])=[CH:35][CH:34]=2)=[N:30][N:29]=1Participants
4
Procedure
A solution of tert-butyl N-[[4-[5-[3-[bis(tert-butoxycarbonyl)amino]-6-(3-propanoyl-3,7-diazaspiro[4.4]nonan-7-yl)pyrazin-2-yl]-1,3,4-oxadiazol-2-yl]phenyl]methyl]-N-methyl-carbamate (129 mg, 0.17 mmol) in dioxane (0.3 mL) was treated with a solution of hydrogen chloride (423 μL of 4 M, 1.7 mmol) in dioxane and the reaction mixture was allowed to stir for 40 minutes. The solvents were removed under reduced pressure and the residue was dissolved in DMF (1 mL) and purified by reverse phase HPLC using (10-99% ACN/H2O (5 mM HCl modifier)) to yield 1-(7-(5-amino-6-(5-(4-((methylamino)methyl)phenyl)-1,3,4-oxadiazol-2-yl)pyrazin-2-yl)-2,7-diazaspiro[4.4]nonan-2-yl)propan-1-one. 1H NMR (400 MHz, DMSO-d6) d 9.44 (s, 2H), 8.13 (dd, J=8.3, 2.4 Hz, 2H), 7.91 (t, J=4.5 Hz, 1H), 7.81 (d, J=7.5 Hz, 2H), 4.26-4.20 (m, 2H), 3.58 (dt, J=13.6, 6.8 Hz, 3H), 3.51-3.29 (m, 5H), 2.57 (t, J=5.3 Hz, 3H), 2.24 (dt, J=15.1, 7.5 Hz, 2H), 1.94 (ddt, J=32.7, 13.2, 6.6 Hz, 4H), 0.99 (dd, J=16.5, 7.5 Hz, 3H). LC/MS m/z 463.5 [M+H]+.