Triethylamine → 6-chloro-N-methoxy-N-methylpyridazine-3-carboxamide

HRID 1046068Notes

Reaction equation

HRID 1046068 reaction equation
[Cl:1][C:2]1[N:7]=[N:6][C:5]([C:8]([OH:10])=O)=[CH:4][CH:3]=1.ClC(Cl)(OC(=O)OC(Cl)(Cl)Cl)Cl.CCN(CC)CC.Cl.[CH3:31][NH:32][O:33][CH3:34]>C(Cl)Cl>[Cl:1][C:2]1[N:7]=[N:6][C:5]([C:8]([N:32]([O:33][CH3:34])[CH3:31])=[O:10])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 94429TriphosgeneHCID 64157626-chloropyridazine-3-carboxylic Acid

Product 1

HCID 584852976-chloro-N-methoxy-N-methylpyridazine-3-carboxamideYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 6-chloropyridazine-3-carboxylic acid (12.5 g, 0.078 mol) in CH2Cl2 (80 mL) at 0° C. were added triphosgene (11.6 g, 0.039 mol), Et3N (55 mL, 0.4 mol), and N,O-dimethylhydroxylamine hydrochloride (7.6 g, 0.078 mol). The reaction mixture was stirred at room temperature for 2 h. The salt was filtered, after removal of the solvent in vacuo, the residue was purified by column chromatography to afford 6-chloro-N-methoxy-N-methylpyridazine-3-carboxamide (13.5 g, 86%). 1H NMR (DMSO-d6, 400 MHz): δ 8.08 (d, J=9.2 Hz, 1H), 8.06 (d, J=9.2 Hz, 1H), 3.33 (s, 3H), 8.06 (s, 3H).

Workup

  1. filtrationThe salt was filtered
  2. customafter removal of the solvent in vacuo
  3. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-d97943aad7044b45b0b0538e12841e99
Source dataset
uspto-grants-2013_10
Patent number
US08569292B2

Reaction notes

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