Methylamine → HCID 86710340, compound

HRID 1398343Notes

Reaction equation

HRID 1398343 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[C:9]=2[CH:22]=O)=[C:4]([F:24])[CH:3]=1.[CH3:25][NH2:26]>C(O)C>[F-:24].[C:17]([O:16][C:15]([NH:14][C:10]1[N:11]=[CH:12][CH:13]=[C:8]2[C:9]=1[CH:22]=[N+:26]([CH3:25])[C:4]1[CH:3]=[C:2]([Cl:1])[CH:7]=[CH:6][C:5]2=1)=[O:21])([CH3:20])([CH3:19])[CH3:18]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 86695909HCID 86695909, compound

Product 1

HCID 86710340HCID 86710340, compoundYield 84.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of tert-butyl (4-(4-chloro-2-fluorophenyl)-3-formylpyridin-2-yl)carbamate (700 mg, 1.996 mmol) in ethanol (10 mL) at 0° C. was added methylamine (8M in EtOH) (620 mg, 2.49 mL, 19.96 mmol) and the reaction was stirred at rt for 5 h. After the consumption of starting material, solvent was removed under reduced pressure. The residue was washed with hexane (50 mL) and the solid so obtained was dried under vacuum to yield the fluoride salt of 4-((tert-butoxycarbonyl)amino)-8-chloro-6-methylbenzo[c][2,7]naphthyridin-6-ium fluoride (900 mg, 1.69 mmol, 84% yield) as a yellow solid. LC/MS (ESI) m/e 344.2 [(M)+, calcd for C18H19ClN3O2 344.1]; LC/MS retention time (method C): tR=1.90 min.

Workup

  1. customAfter the consumption of starting material, solvent
  2. customwas removed under reduced pressure
  3. washThe residue was washed with hexane (50 mL)
  4. customthe solid so obtained
  5. customwas dried under vacuum

Sources & evidence

ORD record
ord-88d94bfdfca043b6bad12d0dcf49bb17
Source dataset
uspto-grants-2014_12
Patent number
US08901305B2

Reaction notes

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