Thionyl Chloride → HCID 118023997, compound

HRID 2205071Notes

Reaction equation

HRID 2205071 reaction equation
S(Cl)(Cl)=O.[CH3:5][N:6]1[C:15](=[O:16])[C:14]2[N:13]=[CH:12][CH:11]=[CH:10][C:9]=2[CH:8]=[C:7]1[C:17]([OH:19])=O.[CH3:20][N:21]1[C:25]([NH2:26])=[N:24][N:23]=[N:22]1>N1C=CC=CC=1>[CH3:5][N:6]1[C:15](=[O:16])[C:14]2[N:13]=[CH:12][CH:11]=[CH:10][C:9]=2[CH:8]=[C:7]1[C:17]([NH:26][C:25]1[N:21]([CH3:20])[N:22]=[N:23][N:24]=1)=[O:19]

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 1384921-methyl-1H-tetrazol-5-amineHCID 118023916HCID 118023916, compound

Product 1

HCID 118023997HCID 118023997, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

At 0° C., 114 mg (0.96 mmol) of thionyl chloride are added to 150 mg (0.74 mmol) of 7-methyl-1,7-naphthyridin-8(7H)-one-6-carboxylic acid and 110 mg (1.1 mmol) of 1-methyl-5-aminotetrazole in 3 ml of pyridine. The mixture is stirred at RT for 16 h. The reaction is then quenched with a little water, the pyridine is evaporated and the residue is purified by HPLC. Yield 27 mg (13%).

Workup

  1. customThe reaction is then quenched with a little water
  2. customthe pyridine is evaporated
  3. customthe residue is purified by HPLC

Sources & evidence

ORD record
ord-735480bd58074156931baba2ddaadc7a
Source dataset
uspto-grants-2016_06
Patent number
US09370184B2

Reaction notes

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