Cesium carbonate → HCID 59286554, compound

HRID 1876041Notes

Reaction equation

HRID 1876041 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.[N:14]1([C:19]2[N:24]=[CH:23][N:22]=[C:21]([N:25]=[C:26](SC)SC)[CH:20]=2)[CH:18]=[CH:17][N:16]=[CH:15]1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[N:14]1([C:19]2[N:24]=[CH:23][N:22]=[C:21]([NH:25][C:26]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)[CH:20]=2)[CH:18]=[CH:17][N:16]=[CH:15]1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 59286655HCID 59286655, compoundHCID 66724709(S)-3-(aminomethyl)quinuclidin-3-ol dihydrochloride

Product 1

HCID 59286554HCID 59286554, compoundYield 85.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of (S)-3-(aminomethyl)quinuclidin-3-ol dihydrochloride (419 mg, 1.8 mmol), dimethyl 6-(1H-imidazol-1-yl)pyrimidin-4-ylcarbonimidodithioate (404 mg, 1.5 mmol), and cesium carbonate (1.24 g, 3.8 mmol) was stirred in DMF (3.8 mL) at 75° C. for 2 h. The reaction was concentrated and purified by flash chromatography on a 40 g silica gel cartridge with 0 to 3% [9:1 MeOH/NH4OH] in CHCl3 to yield (R)—N-(6-(1H-imidazol-1-yl)pyrimidin-4-yl)-4H-1′-azaspiro[oxazole-5,3′-bicyclo[2.2.2]octan]-2-amine (417 mg, 83% yield). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 9.40 (1H, br. s.), 8.60 (1H, d, J=1.01 Hz), 8.37 (1H, t, J=1.01 Hz), 7.55 (1H, t, J=1.39 Hz), 7.16 (1H, dd, J=1.39, 0.88 Hz), 6.84 (1H, br. s.), 3.98 (1H, d, J=9.57 Hz), 3.64 (1H, d, J=9.57 Hz), 3.34 (1H, dd, J=14.98, 1.64 Hz), 2.69-3.04 (5H, m), 2.08-2.21 (2H, m), 1.67-1.78 (1H, m), 1.43-1.62 (2H, m). LCMS: RT=0.26 min, MH+=326.2.

Workup

  1. concentrationThe reaction was concentrated
  2. custompurified by flash chromatography on a 40 g silica gel cartridge with 0 to 3% [9:1 MeOH/NH4OH] in CHCl3

Sources & evidence

ORD record
ord-958570e37d3b4425ae1fa55af0aa3a1d
Source dataset
uspto-grants-2012_11
Patent number
US08309577B2

Reaction notes

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