Cesium carbonate → HCID 59286566, compound

HRID 1876013Notes

Reaction equation

[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[C:7]1[N:12]=[CH:11][N:10]=[C:9]([N:13]=[C:14](SC)SC)[CH:8]=1.C([O-])([O-])=[O:20].[Cs+].[Cs+].Cl.Cl.[NH2:27][CH2:28][C@@:29]1([OH:37])[CH:34]2[CH2:35][CH2:36][N:31]([CH2:32][CH2:33]2)[CH2:30]1>CN(C)C=O.C(OCC)(=O)C>[OH-:20].[NH4+:1].[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[C:7]1[N:12]=[CH:11][N:10]=[C:9]([NH:13][C:14]2[O:37][C@:29]3([CH2:28][N:27]=2)[CH:34]2[CH2:35][CH2:36][N:31]([CH2:32][CH2:33]2)[CH2:30]3)[CH:8]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of dimethyl 6-(pyrazin-2-yl)pyrimidin-4-ylcarbonimidodithioate (0.139 g, 0.501 mmol), Cs2CO3 (0.408 g, 1.253 mmol) and (S)-3-(aminomethyl)quinuclidin-3-ol dihydrochloride (0.115 g, 0.501 mmol) in N,N-dimethylformamide (10 ml) was heated at 80° C. for 3 h. The mixture was concentrated and purified on silica gel using 0-10% 9.5:0.5 methanol:ammonium hydroxide in ethyl acetate to give (R)—N-(6-(pyrazin-2-yl)pyrimidin-4-yl)-4H-1′-azaspiro[oxazole-5,3′-bicyclo[2.2.2]octan]-2-amine as an off-white solid (0.066 g, 0.194 mmol, 39%). 1H NMR (400 MHz, MeOD) δ ppm 9.46 (1H, d, J=1.51 Hz), 8.83 (1H, d, J=1.26 Hz), 8.67-8.72 (1H, m), 8.66 (1H, d, J=2.52 Hz), 7.77 (1H, br. s.), 4.05 (1H, d, J=10.32 Hz), 3.75 (1H, d, J=10.32 Hz), 3.18-3.26 (1H, m), 3.04-3.15 (1H, m), 2.87-3.00 (2H, m), 2.70-2.85 (2H, m), 2.04-2.19 (2H, m), 1.54-1.83 (3H, m). MS (LC/MS) R.T.=0.97; [M+H]+=338.29.

Workup

concentrationThe mixture was concentrated
custompurified on silica gel using 0-10% 9.5:0.5 methanol

Sources & evidence

ORD record: ord-b9f1b8d15f9649ab9756a2fa0c3fb5ac
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08309577B2

Reaction notes

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