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

HRID 475460Notes

Reaction equation

HRID 475460 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-one

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 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-2bee65b49def45ff98cd72ab56395666
Source dataset
uspto-grants-2014_01
Patent number
US08637552B2

Reaction notes

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