Hydrochloric Acid → trans-2-(2-(6-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)-2-methylpyrimidin-4-yl)cyclopropyl)benzo[d]thiazole dihydrochloric acid salt
Reaction equation
[CH3:1][C:2]1[N:6]=[C:5]([CH3:7])[N:4]([C:8]2[N:13]=[C:12]([CH3:14])[N:11]=[C:10]([C@@H:15]3[CH2:17][C@H:16]3[C:18]3[S:19][C:20]4[CH:26]=[CH:25][CH:24]=[CH:23][C:21]=4[N:22]=3)[CH:9]=2)[N:3]=1.[ClH:27]>C(Cl)Cl>[ClH:27].[ClH:27].[CH3:1][C:2]1[N:6]=[C:5]([CH3:7])[N:4]([C:8]2[N:13]=[C:12]([CH3:14])[N:11]=[C:10]([C@@H:15]3[CH2:17][C@H:16]3[C:18]3[S:19][C:20]4[CH:26]=[CH:25][CH:24]=[CH:23][C:21]=4[N:22]=3)[CH:9]=2)[N:3]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of trans-2-(2-(6-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)-2-methylpyrimidin-4-yl)cyclopropyl)benzo[d]thiazole (2-2) (26.0 mg, 72 μmol) in CH2Cl2 (0.2 mL) was added hydrochloric acid (4.0 M in 1,4-dioxane, 36.0 μL, 0.144 mmol, 2.0 eq.) and after 10 minutes the solvent was removed to afford trans-2-(2-(6-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)-2-methylpyrimidin-4-yl)cyclopropyl)benzo[d]thiazole dihydrochloric acid salt (2-3) as an off-white solid. 1H NMR (300 MHz, DMSO-d6) δ 8.00 (br d, 1H, J=7.8 Hz), 7.89 (br d, 1H, J=7.8 Hz), 7.72 (s, 1H), 7.47 (td, 1H, J=7.8, 1.2 Hz), 7.38 (td, 1H, J=7.8, 1.2 Hz), 3.13 (ddd, 1H, J=8.7, 6.0, 4.0 Hz), 3.02 (ddd, 1H, J=8.7, 6.0, 4.0 Hz), 2.79 (s, 3H), 2.63 (s, 3H), 2.29 (s, 3H), 2.03-1.90 (m, 2H). LRMS m/z (M+H+) 363 found, 363 required. m.p. 194-195° C. dec.
Workup
- customafter 10 minutes the solvent was removed
Sources & evidence
- ORD record
- ord-6448c66b17b94e4dba0a9ea17943b93f
- Source dataset
- uspto-grants-2015_12
- Patent number
- US09200001B2
Reaction notes
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