Cesium carbonate → HCID 58087958, compound
Reaction equation
Cl.Cl.[NH2:3][CH2:4][C@@:5]1([OH:13])[CH:10]2[CH2:11][CH2:12][N:7]([CH2:8][CH2:9]2)[CH2:6]1.C([O-])([O-])=O.[Cs+].[Cs+].[N:20]([C:23]1[N:28]=[CH:27][N:26]=[C:25]([C:29]2[CH:30]=[N:31][C:32]([O:35][CH3:36])=[N:33][CH:34]=2)[CH:24]=1)=[C:21]=S.C(N=C=NC(C)C)(C)C>CN(C)C=O>[CH3:36][O:35][C:32]1[N:33]=[CH:34][C:29]([C:25]2[CH:24]=[C:23]([NH:20][C:21]3[O:13][C@:5]4([CH2:4][N:3]=3)[CH:10]3[CH2:9][CH2:8][N:7]([CH2:12][CH2:11]3)[CH2:6]4)[N:28]=[CH:27][N:26]=2)=[CH:30][N:31]=1Participants
Procedure
To (S)-3-(aminomethyl)quinuclidin-3-ol dihydrochloride (0.093 g, 0.41 mmol) in N,N-dimethylformamide (20 mL) was added Cs2CO3 (0.33 g, 1 mmol)) and 6-isothiocyanato-2′-methoxy-4,5′-bipyrimidine (0.1 g, 0.41 mmol). The suspension was stirred at room temperature for 30 minutes. N,N′-Diisopropylcarbodiimide (0.19 mL, 1.2 mmol) was then added and the mixture was stirred at room temperature for 18 hours. The mixture was concentrated and purified by silica gel chromatography (5-25% [9:1 methanol:ammonium hydroxide]-ethyl acetate) to afford (R)—N-(2′-methoxy-4,5′-bipyrimidin-6-yl)-4H-1′-azaspiro[oxazole-5,3′-bicyclo[2.2.2]octan]-2-amine (0.072 g, 0.188 mmol, 46% yield) as an off-white solid. 1H NMR (400 MHz, MeOD) δ ppm 9.19 (2 H, s), 8.80 (1 H, d), 7.24 (1 H, br. s.), 4.00-4.09 (4 H, m), 3.76 (1 H, d), 3.23 (1 H, s), 3.08-3.15 (1 H, m), 2.72-3.04 (4 H, m), 1.97-2.22 (2 H, m), 1.38-1.85 (3 H, m). R.T.=1.22; [M+H]+=368.22.
Workup
- stirringthe mixture was stirred at room temperature for 18 hours
- concentrationThe mixture was concentrated
- custompurified by silica gel chromatography (5-25% [9:1 methanol:ammonium hydroxide]-ethyl acetate)
Sources & evidence
- ORD record
- ord-dbfa356c09d44b6291ac202a938b6eb9
- Source dataset
- uspto-grants-2011_01
- Patent number
- US07863291B2
Reaction notes
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