Methylamine → 2-Acetamido-8-chloro-6-methylbenzo[c][2,7]naphthyridin-6-ium fluoride

HRID 1398353Notes

Reaction equation

HRID 1398353 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([CH:14]=O)=[CH:12][N:11]=[C:10]([NH:16][C:17](=[O:19])[CH3:18])[CH:9]=2)=[C:4]([F:20])[CH:3]=1.[CH3:21][NH2:22]>ClCCl>[F-:20].[C:17]([NH:16][C:10]1[CH:9]=[C:8]2[C:13](=[CH:12][N:11]=1)[CH:14]=[N+:22]([CH3:21])[C:4]1[CH:3]=[C:2]([Cl:1])[CH:7]=[CH:6][C:5]2=1)(=[O:19])[CH3:18]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 86695932N-(4-(4-chloro-2-fluorophenyl)-5-formylpyridin-2-yl)acetamide

Product 1

HCID 867103462-Acetamido-8-chloro-6-methylbenzo[c][2,7]naphthyridin-6-ium fluorideYield 93.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of N-(4-(4-chloro-2-fluorophenyl)-5-formylpyridin-2-yl)acetamide (0.39 g, 1.332 mmol) and 4 Å molecular sieves (50 mg) in dichloromethane (35 mL) at 0° C. was added methyl amine (8M in EtOH, 0.041 g, 0.166 mL, 1.332 mmol) dropwise and the reaction was stirred at rt overnight (12 h). The reaction mixture was diluted with DCM (40 mL) and filtered through a bed of diatomaceous earth (Celite®). The filtrate was concentrated under reduced pressure to afford 2-acetamido-8-chloro-6-methylbenzo[c][2,7]naphthyridin-6-ium fluoride (450 mg, 1.24 mmol, 93% yield) as a yellow solid that was used in the next step without purification. LC/MS (ESI) m/e 286.1 [(M)+, calcd for C15H13ClN3O 286.1]; LC/MS retention time (Method D): tR=0.71 min.

Workup

  1. filtrationfiltered through a bed of diatomaceous earth (Celite®)
  2. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-73f6d047097d4459b3816b9c2180cded
Source dataset
uspto-grants-2014_12
Patent number
US08901305B2

Reaction notes

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