Sodium Thiosulfate → HCID 178510421, compound

HRID 536943Notes

Reaction equation

HRID 536943 reaction equation
[C:1]1([C:7]2[CH:12]=[C:11]([C:13]3([CH2:19][OH:20])[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)[CH:10]=[CH:9][C:8]=2[NH:21][C:22]([C:24]2[NH:25][CH:26]=[C:27]([C:29]#[N:30])[N:28]=2)=[O:23])[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C([O-])(O)=O.[Na+].[O-]S([O-])(=S)=O.[Na+].[Na+]>C(Cl)Cl.O>[C:1]1([C:7]2[CH:12]=[C:11]([C:13]3([CH:19]=[O:20])[CH2:14][CH2:15][O:16][CH2:17][CH2:18]3)[CH:10]=[CH:9][C:8]=2[NH:21][C:22]([C:24]2[NH:25][CH:26]=[C:27]([C:29]#[N:30])[N:28]=2)=[O:23])[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1

Participants

7

Reactant 4

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 178510422HCID 178510422, compound

Product 1

HCID 178510421HCID 178510421, compoundYield 60.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 4-cyano-1H-imidazole-2-carboxylic acid [2-cyclohex-1-enyl-4-(4-hydroxymethyl-tetrahydro-pyran-4-yl)-phenyl]-amide (as prepared in Example 20, 75.4 mg, 0.185 mmol), Dess-Martin periodinane (157 mg, 0.369 mmol) and NaHCO3 (155 mg, 1.85 mmol) in 3 mL of DCM was stirred at 0° C. for 0.5 h, at RT for 1 h. To the reaction was added 2 mL of 10% Na2S2O3 and the resulting mixture was stirred vigorously for 5 min. The mixture was treated with 20 mL of H2O and extracted with EtOAc (2×40 mL). The combined organic layers were washed with saturated NaHCO3 aqueous solution (10 mL), H2O (10 mL) and brine (10 mL). After drying over Na2SO4 and concentrating in vacuo, the residue was purified by silica gel chromatography (10-20% EtOAc/DCM) to afford the title compound (45 mg, 60%) as a white solid. Mass spectrum (ESI, m/z): Calcd. for C23H24N4O3, 405.2 (M+H). found 405.1.

Workup

  1. stirringthe resulting mixture was stirred vigorously for 5 min
  2. extractionextracted with EtOAc (2×40 mL)
  3. washThe combined organic layers were washed with saturated NaHCO3 aqueous solution (10 mL), H2O (10 mL) and brine (10 mL)
  4. dry with materialAfter drying over Na2SO4
  5. concentrationconcentrating in vacuo
  6. customthe residue was purified by silica gel chromatography (10-20% EtOAc/DCM)

Sources & evidence

ORD record
ord-633ea8793b0c4537b1f39a927652f526
Source dataset
uspto-grants-2014_10
Patent number
US08859602B2

Reaction notes

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