Trimethylsilyldiazomethane → HCID 22346362, compound

HRID 897320Notes

Reaction equation

HRID 897320 reaction equation
[F:1][C:2]1[CH:24]=[CH:23][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:19]([OH:20])=[C:18]3[C:13]([CH:14]=[CH:15][CH:16]=[N:17]3)=[C:12]([NH:21][CH3:22])[N:11]=2)=[O:9])=[CH:4][CH:3]=1.[CH3:25][Si](C=[N+]=[N-])(C)C>CO.C(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:19]([O:20][CH3:25])=[C:18]3[C:13]([CH:14]=[CH:15][CH:16]=[N:17]3)=[C:12]([NH:21][CH3:22])[N:11]=2)=[O:9])=[CH:23][CH:24]=1

Participants

5

Reactant 2

HCID 167693Trimethylsilyldiazomethane2×HCID 22346269HCID 22346269, compound

Product 1

HCID 22346362HCID 22346362, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a suspension of N-(4-fluorobenzyl)-8-hydroxy-5-(methylamino)-1,6-naphthyridine-7-carboxamide (2.65 g, 8.12 mmol) in methanol (50 mL) and CH2Cl2 (20 mL) was added trimethylsilyldiazomethane (12.1 ml of a 2M solution in hexanes, 24.4 mmol) and the mixture was stirred for 16 hr at rt. Additional trimethylsilyldiazomethane (24.0 ml of a 2M solution in hexanes, 48 mmol) was added and the reaction was stirred for 16 hr. The reaction was quenched by the addition of acetic acid (2 mL) and the solvent was evaporated in vacuo. The residue was purified by flash chromatography eluting with MeOH/CH2Cl2 (5-15% gradient elution), to afford the title compound.

Workup

  1. stirringthe reaction was stirred for 16 hr
  2. customThe reaction was quenched by the addition of acetic acid (2 mL)
  3. customthe solvent was evaporated in vacuo
  4. customThe residue was purified by flash chromatography
  5. washeluting with MeOH/CH2Cl2 (5-15% gradient elution)

Sources & evidence

ORD record
ord-15e572bf5d014ef2bc44b7f7af929762
Source dataset
uspto-grants-2005_07
Patent number
US06921759B2

Reaction notes

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