Carbon Dioxide → HCID 11210875, compound

HRID 916653Notes

Reaction equation

HRID 916653 reaction equation
[F:1][C:2]1[C:3]([C:8]2[N:9]([CH2:13][C:14]3[N:19]=[CH:18][N:17]4[N:20]=[C:21]([CH2:23]O)[N:22]=[C:16]4[C:15]=3[CH2:25][CH2:26][CH3:27])[CH:10]=[CH:11][N:12]=2)=[N:4][CH:5]=[CH:6][CH:7]=1.COCCN(S(F)(F)[F:38])CCOC.C([O-])(O)=O.[Na+].C(=O)=O>ClCCl>[F:38][CH2:23][C:21]1[N:22]=[C:16]2[N:17]([CH:18]=[N:19][C:14]([CH2:13][N:9]3[CH:10]=[CH:11][N:12]=[C:8]3[C:3]3[C:2]([F:1])=[CH:7][CH:6]=[CH:5][N:4]=3)=[C:15]2[CH2:25][CH2:26][CH3:27])[N:20]=1

Participants

6

Reactant 4

HCID 280Carbon DioxideHCID 516892Sodium BicarbonateHCID 2734690(Bis(2-methoxyethyl)amino)sulfur trifluorideHCID 57503253HCID 57503253, compound2×

Product 1

HCID 11210875HCID 11210875, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution {7-[2-(3-fluoro-pyridin-2-yl)-imidazol-1-ylmethyl]-8-propyl-[1,2,4]triazolo[1,5-c]pyrimidin-2-yl}-methanol (compound 223, below) (31 mg, 0.08 mmol) in dichloromethane (5 mL) is added bis(2-methoxyethyl)aminosulfur trifluoride (0.2 ml, 50% in THF) at room temperature under N2. The mixture is stirred for two hours, and is poured into saturated NaHCO3 (10 mL), and after CO2 evolution ceases it is extracted into dichloromethane, dried (MgSO4), filtered and evaporated in vacuo. PTLC by 5% MeOH/dichloromethane gives the pure product (157). 1H NMR: 0.98 (3H, t, J=5.4 Hz), 1.67 (2H, m), 2.99 (2H, m), 5.69 (2H, d, J=35.1 Hz), 5.88 (2H, s), 7.22 (1H, s), 7.22–7.31 (2H, m), 7.54 (1H, t, J=6.0 Hz), 8.39 (1H, s), 9.13 (1H, s). LCMS (M+1) 370.20.

Workup

  1. extractionis extracted into dichloromethane
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-9419b5f46f4742a2a361aa70ac3f6d8c
Source dataset
uspto-grants-2007_09
Patent number
US07271170B2

Reaction notes

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