Trimethylsilyldiazomethane → HCID 117667318, compound

HRID 712634Notes

Reaction equation

HRID 712634 reaction equation
[C:1]([N:4]1[C:13]2[N:12]=[CH:11][C:10]([C:14]3[CH:22]=[N:21][CH:20]=[CH:19][C:15]=3[C:16]([OH:18])=[O:17])=[CH:9][C:8]=2[CH2:7][CH2:6][CH2:5]1)(=[O:3])[NH2:2].[CH3:23][Si](C=[N+]=[N-])(C)C>C1(C)C=CC=CC=1.CO>[CH3:23][O:17][C:16](=[O:18])[C:15]1[CH:19]=[CH:20][N:21]=[CH:22][C:14]=1[C:10]1[CH:11]=[N:12][C:13]2[N:4]([C:1](=[O:3])[NH2:2])[CH2:5][CH2:6][CH2:7][C:8]=2[CH:9]=1

Participants

4

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 117667239HCID 117667239, compound

Product 1

HCID 117667318HCID 117667318, compoundYield 39.1%

Reagents, catalysts & solvents 1

HCID 21867641Toluene methanolSolvent

Procedure

To a solution of 3-(8-carbamoyl-5,6,7,8-tetrahydro-[1,8]naphthyridin-3-yl)-isonicotinic acid (80 mg, 0.27 mmol) in 8.0 mL of toluene/MeOH 1:1 mixture is added 2.0 M trimethylsilyl-diazomethane (0.20 mL, 0.40 mmol) under N2 atmosphere. The reaction solution is stirred at room temperature for 16 hrs. The solvent is removed and the residue is purified by preparative HPLC to give 33 mg of the titled product.

Workup

  1. customThe solvent is removed
  2. customthe residue is purified by preparative HPLC

Sources & evidence

ORD record
ord-1231e3fb93e64b6caa32a6a182abb8ae
Source dataset
uspto-grants-2015_11
Patent number
US09181272B2

Reaction notes

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