Cesium carbonate → HCID 58088074, compound

HRID 250126Notes

Reaction equation

HRID 250126 reaction equation
[NH2:1][CH2:2][C@@:3]1([OH:11])[CH:8]2[CH2:9][CH2:10][N:5]([CH2:6][CH2:7]2)[CH2:4]1.CCN(C(C)C)C(C)C.C([O-])([O-])=O.[Cs+].[Cs+].[Cl:27][C:28]1[CH:29]=[CH:30][C:31]2[O:35][C:34]([N:36]=[C:37](SC)SC)=[N:33][C:32]=2[CH:42]=1>CN(C=O)C>[Cl:27][C:28]1[CH:29]=[CH:30][C:31]2[O:35][C:34]([NH:36][C:37]3[O:11][C@:3]4([CH2:2][N:1]=3)[CH:8]3[CH2:7][CH2:6][N:5]([CH2:10][CH2:9]3)[CH2:4]4)=[N:33][C:32]=2[CH:42]=1

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 81531DiisopropylethylamineHCID 58088043HCID 58088043, compoundHCID 86635293HCID 86635293, compound

Product 1

HCID 58088074HCID 58088074, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A 10 ml vial was charged with (S)-3-(aminomethyl)quinuclidin-3-ol.2HCl salt (106 mg, 0.550 mmol), DMF (2 ml), DIEA (0.096 mL, 0.550 mmol), and Cs2CO3(358 mg, 1.100 mmol) at room temperature, followed by dimethyl 5-chlorobenzo[d]oxazol-2-ylcarbonimidodithioate (150 mg, 0.550 mmol). The resulting suspension was stirred at room temperature for 1 hr. LC/MS then indicated consumption of starting material. The reaction mixture was diluted with MeOH and purified by preparative HPLC to afford the expected product, (R)—N-(5-chlorobenzo[d]oxazol-2-yl)-4H-1′-azaspiro[oxazole-5,3′-bicyclo[2.2.2]octan]-2-amine (106.5 mg, 0.3 mmol, 53.0% yield), as a white solid. 1H NMR (400 MHz, Acetone-d6) δ ppm 2.08-2.30 (m, 3H) 2.35-2.48 (m, 1H) 2.60-2.73 (m, 1H) 3.48 (qd, J=7.53, 7.28 Hz, 3H) 3.54-3.68 (m, 1H) 3.79-4.00 (m, 2H) 4.18 (d, J=10.54 Hz, 1H) 4.35 (d, J=10.54 Hz, 1H) 7.19 (dd, J=8.53, 2.01 Hz, 1H) 7.30-7.47 (m, 2H) 9.10 (br. s., 1H). MS(LC/MS) R.T.=1.56; [M+H]+=333.13.

Workup

  1. customat room temperature
  2. customconsumption of starting material
  3. additionThe reaction mixture was diluted with MeOH
  4. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-4dc39f7d983b43f3aea30fce7e7ff90e
Source dataset
uspto-grants-2011_01
Patent number
US07863291B2

Reaction notes

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