Tetrahydrofuran → HCID 86673126, compound

HRID 871837Notes

Reaction equation

HRID 871837 reaction equation
Cl[C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[S:9])=[CH:6][N:5]=[C:4]([CH3:13])[CH:3]=1.ClC1C(C(OCC)=S)=C(C)[N:18]=C(C)C=1.C1COCC1.O1CCOCC1>C(N(CC)CC)C>[NH2:18][C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[S:9])=[CH:6][N:5]=[C:4]([CH3:13])[CH:3]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 312751,4-DioxaneHCID 86673127HCID 86673127, compoundHCID 86673128HCID 86673128, compound

Product 1

HCID 86673126HCID 86673126, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

In accordance with Scheme 1 below, ethyl 4-chloro-2-methylthiopyridine-5-carboxylate (II with A=CH) (prepared according to Todd et al., J. Amer. Chem. Soc. (1943), 65, 350-354; Pesson, M., Eur. J. Med. Chem. (1974), 9(6), 585-590; Shadbolt, R., J. Chem. Soc. (1967), 13, 1172-1178) or ethyl 4-chloro-6-methyl-2-methylthiopyridine-5-carboxylate (II with A=C-Me) (prepared according to the method described in WO 2005/105 801) is reacted with an amine of formula R5—NH2 (in which R5 is as defined previously in relation to formula (I) according to the invention) in an organic solvent such as THF or dioxane, and in the presence of an organic base, for example triethylamine, at room temperature, according to the method described by D. Boschelli et al. in J. Med. Chem. (1998), 41, 4365-4377, to give an ethyl 4-amino-2-methylthiopyridine-5-carboxylate derivative of formula (III).

Workup

  1. customprepared
  2. customat room temperature

Sources & evidence

ORD record
ord-fe38fe2bd3b845db8c78fa9fc6102314
Source dataset
uspto-grants-2015_03
Patent number
US08975250B2

Reaction notes

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