Sodium Thiosulfate → HCID 59313180, compound

HRID 73497Notes

Reaction equation

HRID 73497 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:27])[C:7]=1[CH2:8][C:9]([C:11]1[N:16]2[N:17]=[C:18]([C:20]3([CH2:23][OH:24])[CH2:22][CH2:21]3)[N:19]=[C:15]2[C:14]([O:25][CH3:26])=[CH:13][CH:12]=1)=[O:10].C([O-])(O)=O.[Na+].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[O-]S([O-])(=S)=O.[Na+].[Na+]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:27])[C:7]=1[CH2:8][C:9]([C:11]1[N:16]2[N:17]=[C:18]([C:20]3([CH:23]=[O:24])[CH2:21][CH2:22]3)[N:19]=[C:15]2[C:14]([O:25][CH3:26])=[CH:13][CH:12]=1)=[O:10]

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium Bicarbonate2×HCID 251148032-(3,5-Dichloro-pyridin-4-yl)-1-[2-(1-hydroxymethyl-cyclopropyl)-8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-5-yl]-ethanone

Product 1

HCID 59313180HCID 59313180, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-(3,5-Dichloro-pyridin-4-yl)-1-[2-(1-hydroxymethyl-cyclopropyl)-8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-5-yl]-ethanone obtained in example 6 (154 mg, 0.38 mmol) was dissolved in DCM (5 mL) and treated with NaHCO3 (127 mg, 1.51 mmol) and Dess-Martin periodinane (321 mg, 0.756 mmol). The suspension was stirred for 30 min at rt and then treated with a 50 mL of a 1:1 mixture of Na2S2O3 (sat., aq.) and NaHCO3 (sat., aq.). The reaction mixture was then extracted with EtOAc (2×25 mL). The combined organic phases were washed with brine and dried over Na2SO4, filtered and concentrated in vacuo. Yield 156 mg of slightly yellow solid, which was used without further purification.

Workup

  1. extractionThe reaction mixture was then extracted with EtOAc (2×25 mL)
  2. washThe combined organic phases were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customYield 156 mg of slightly yellow solid, which was used without further purification

Sources & evidence

ORD record
ord-4bdf42847d4d425fb0a8efdd087d4f92
Source dataset
uspto-grants-2014_09
Patent number
US08829190B2

Reaction notes

Loading…