Isopropylamine → 3-chloro-N-[4-chloro-2-methyl-6-[[(1-methylethyl)amino]-carbonyl]phenyl]-1-(3-chloro-2-pyridinyl)-1H-pyrazole-5-carboxamide

HRID 1409952Notes

Reaction equation

HRID 1409952 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH3:26])[C:5]2[N:10]=[C:9]([C:11]3[N:15]([C:16]4[C:21]([Cl:22])=[CH:20][CH:19]=[CH:18][N:17]=4)[N:14]=[C:13]([Cl:23])[CH:12]=3)[O:8][C:7](=O)[C:6]=2[CH:25]=1.[CH:27]([NH2:30])([CH3:29])[CH3:28].[O:31]1CCCC1>>[Cl:23][C:13]1[CH:12]=[C:11]([C:9]([NH:10][C:5]2[C:6]([C:7]([NH:30][CH:27]([CH3:29])[CH3:28])=[O:31])=[CH:25][C:2]([Cl:1])=[CH:3][C:4]=2[CH3:26])=[O:8])[N:15]([C:16]2[C:21]([Cl:22])=[CH:20][CH:19]=[CH:18][N:17]=2)[N:14]=1

Participants

4

Reactant 3

HCID 6363IsopropylamineHCID 8028TetrahydrofuranHCID 211133906-chloro-2-[3-chloro-(3-chloro-2-pyridinyl)-1H-pyrazol-5-yl]-8-methyl-4H-3,1-benzoxazin-4-one2×

Product 1

HCID 231543163-chloro-N-[4-chloro-2-methyl-6-[[(1-methylethyl)amino]-carbonyl]phenyl]-1-(3-chloro-2-pyridinyl)-1H-pyrazole-5-carboxamide

Conditions

Temperature
60 °C

Procedure

To a solution of 6-chloro-2-[3-chloro-1-(3-chloro-2-pyridinyl)-1H-pyrazol-5-yl]-8-methyl-4H-3,1-benzoxazin-4-one (e.g, the benzoxazinone product of Step E) (6.21 g, 15.21 mmol) in tetrahydrofuran (100 mL) was added isopropylamine (4.23 g, 72.74 mmol) and the reaction mixture was then heated to 60° C., stirred for 1 hour and then cooled to room temperature. The tetrahydrofuran solvent was evaporated under reduced pressure, and the residual solid was purified by chromatography on silica gel to afford the title compound, a compound of the present invention, as a white solid (5.05 g) melting at 173-175° C.

Workup

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

Sources & evidence

ORD record
ord-d210435860c3494896241162293dc620
Source dataset
uspto-grants-2014_12
Patent number
US08921400B2

Reaction notes

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