Methylamine → 3-chloro-1-(3-chloro-2-pyridinyl)-N-[2-chloro-4-cyano-6-[(methylamino)carbonyl]phenyl]-1H-pyrazole-5-carboxamide

HRID 254435Notes

Reaction equation

HRID 254435 reaction equation
[Cl:1][C:2]1[C:11]2[N:10]=[C:9]([C:12]3[N:16]([C:17]4[C:22]([Cl:23])=[CH:21][CH:20]=[CH:19][N:18]=4)[N:15]=[C:14]([Cl:24])[CH:13]=3)[O:8][C:7](=[O:25])[C:6]=2[CH:5]=[C:4]([C:26]#[N:27])[CH:3]=1.[CH3:28][NH2:29]>O1CCCC1>[Cl:24][C:14]1[CH:13]=[C:12]([C:9]([NH:10][C:11]2[C:6]([C:7]([NH:29][CH3:28])=[O:25])=[CH:5][C:4]([C:26]#[N:27])=[CH:3][C:2]=2[Cl:1])=[O:8])[N:16]([C:17]2[C:22]([Cl:23])=[CH:21][CH:20]=[CH:19][N:18]=2)[N:15]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 668575628-chloro-2-[3-chloro-1-(3-chloro-2-pyridinyl)-1H-pyrazol-5-yl]-6-cyano-4H-3,1-benzoxazin-4-one2×

Product 1

HCID 668580073-chloro-1-(3-chloro-2-pyridinyl)-N-[2-chloro-4-cyano-6-[(methylamino)carbonyl]phenyl]-1H-pyrazole-5-carboxamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 8-chloro-2-[3-chloro-1-(3-chloro-2-pyridinyl)-1H-pyrazol-5-yl]-6-cyano-4H-3,1-benzoxazin-4-one (i.e. the cyanobenzoxazinone product of Step C) (187 mg, 0.446 mmol) in tetrahydrofuran (5 mL) was added dropwise methylamine (2.0 M solution in THF, 0.5 mL, 1.0 mmol) and the reaction mixture was stirred for 5 minutes, at which point thin layer chromatography on silica gel confirmed completion of the reaction. The tetrahydrofuran solvent was evaporated under reduced pressure, and the residual solid was purified by chromatography on silica gel to afford 49 mg of the title compound, a compound of the present invention, as a white solid that melted at 197-200° C.

Workup

  1. customThe tetrahydrofuran solvent was evaporated under reduced pressure
  2. customthe residual solid was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-e9c8273e4595465594ae79a9e5a99cf8
Source dataset
uspto-grants-2011_01
Patent number
US07875634B2

Reaction notes

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