Trimethylsilyldiazomethane → HCID 86305712, compound

HRID 712602Notes

Reaction equation

HRID 712602 reaction equation
[C:1]([N:4]1[C:13]2[N:12]=[CH:11][C:10]([C:14]3[CH:15]=[N:16][CH:17]=[C:18]([CH:22]=3)[C:19]([OH:21])=[O:20])=[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:20][C:19](=[O:21])[C:18]1[CH:22]=[C:14]([C:10]2[CH:11]=[N:12][C:13]3[N:4]([C:1](=[O:3])[NH2:2])[CH2:5][CH2:6][CH2:7][C:8]=3[CH:9]=2)[CH:15]=[N:16][CH:17]=1

Participants

4

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 86305668HCID 86305668, compound

Product 1

HCID 86305712HCID 86305712, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 21867641Toluene methanolSolvent

Procedure

To the solution of 5-(8-Carbamoyl-5,6,7,8-tetrahydro-[1,8]naphthyridin-3-yl)-nicotinic acid (100 mg, 0.33 mmol) in 12 mL of toluene/MeOH 3:1 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 solvents are removed in vacuo and the residue is purified by preparative HPLC to give 33 mg of the titled product.

Workup

  1. customThe solvents are removed in vacuo
  2. customthe residue is purified by preparative HPLC

Sources & evidence

ORD record
ord-3562915f81d74c6288e05af5a319de93
Source dataset
uspto-grants-2015_11
Patent number
US09181272B2

Reaction notes

Loading…