N,N-Dimethylglycine → HCID 67263270, compound

HRID 1684938Notes

Reaction equation

HRID 1684938 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5](I)=[CH:4][N:3]=1.[SH:9][C:10]1[CH:11]=[C:12]([CH:16]=[CH:17][CH:18]=1)[C:13]([OH:15])=[O:14].CN(C)CC(O)=O.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>CN(C)C=O.[Cu]I.O>[NH2:1][C:2]1[N:3]=[CH:4][C:5]([S:9][C:10]2[CH:11]=[C:12]([CH:16]=[CH:17][CH:18]=2)[C:13]([OH:15])=[O:14])=[CH:6][CH:7]=1

Participants

8

Reactant 4

HCID 673N,N-DimethylglycineHCID 62657Potassium Phosphate, TribasicHCID 885792-Pyridinamine, 5-iodo-HCID 95737Benzoic acid, 3-mercapto-

Product 1

HCID 67263270HCID 67263270, compoundYield 34.1%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

A procedure described in Syn. Lett. 1254, 2004 was followed. To solution of 2-amino-5-iodopyridine (220 mg, 1 mmol) in dimethyl formamide (2 mL) were added sequentially 3-mercaptobenzoic acid (185 mg, 1.2 mmol), CuI (50 mg), N,N-dimethylglycine (50 mg) and K3PO4 (1.06 g). The mixture was heated to 120° C. for 2 h, cooled to RT and water was added. The solid was filtered and the filtrate was treated with 1N HCl to adjust the solution to pH 4. The solid formed was collected by filtration, dissolved in 1N NaOH and the solution was filtered. The filtrate was purified by RP HPLC eluting with a mixture of methanol in water containing 0.1% TFA to obtain 3-(6-aminopyridin-3-ylthio)benzoic acid (84 mg, 34%). LC/MS; (M+H)+=247.

Workup

  1. temperaturecooled to RT
  2. filtrationThe solid was filtered
  3. additionthe filtrate was treated with 1N HCl
  4. customThe solid formed
  5. filtrationwas collected by filtration
  6. dissolutiondissolved in 1N NaOH
  7. filtrationthe solution was filtered
  8. customThe filtrate was purified by RP HPLC
  9. washeluting with a mixture of methanol in water containing 0.1% TFA

Sources & evidence

ORD record
ord-ea00abd48e8b4f78a24c9ba66e0fe3e0
Source dataset
uspto-grants-2012_04
Patent number
US08148361B2

Reaction notes

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