Isopropylamine → 6-{[2-(3-chloro-pyridin-2-yl)-5-trifluoromethyl-2H-pyrazole-3-carbonyl]-amino}-1H-indole-7-carboxylic acid isopropylamide

HRID 245606Notes

Reaction equation

HRID 245606 reaction equation
[Cl:1][C:2]1[C:3]([N:8]2[C:12]([C:13]3[O:22][C:21](=[O:23])[C:20]4[C:15](=[CH:16][CH:17]=[C:18]5[CH:26]=[CH:25][NH:24][C:19]5=4)[N:14]=3)=[CH:11][C:10]([C:27]([F:30])([F:29])[F:28])=[N:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1.[CH:31]([NH2:34])([CH3:33])[CH3:32]>O1CCCC1>[CH:31]([NH:34][C:21]([C:20]1[C:15]([NH:14][C:13]([C:12]2[N:8]([C:3]3[C:2]([Cl:1])=[CH:7][CH:6]=[CH:5][N:4]=3)[N:9]=[C:10]([C:27]([F:29])([F:28])[F:30])[CH:11]=2)=[O:22])=[CH:16][CH:17]=[C:18]2[C:19]=1[NH:24][CH:25]=[CH:26]2)=[O:23])([CH3:33])[CH3:32]

Participants

4

Reactant 2

HCID 6363IsopropylamineHCID 1361760267-[2-(3-chloro-pyridin-2-yl)-5-trifluoromethyl-2H-pyrazol-3-yl]-1H-8-oxa-1,6-diaza-cyclopenta[a]naphthalen-9-one

Product 1

HCID 579901666-{[2-(3-chloro-pyridin-2-yl)-5-trifluoromethyl-2H-pyrazole-3-carbonyl]-amino}-1H-indole-7-carboxylic acid isopropylamideYield 16%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 110 mg (0.25 mmol) of the crude 7-[2-(3-chloro-pyridin-2-yl)-5-trifluoromethyl-2H-pyrazol-3-yl]-1H-8-oxa-1,6-diaza-cyclopenta[a]naphthalen-9-one in 2.5 mL of anhydrous tetrahydrofuran, under Argon, is added 0.07 mL (0.77 mmol) of isopropylamine. The reaction is stirred during 5 hours at ambient temperature and then quenched with an aqueous saturated solution of ammonium chloride. The product is extracted twice with ethyl acetate and the combined organic phases are dried on Na2SO4, filtrated and the solvent is evaporated. After purification by flash chromatography on silica gel with hexanes and ethyl acetate as eluents and a preparative thin layer chromatography, 18.5 mg (0.04 mmol, 16%) of a white solid are obtained; LC/MS:513/515 (M+Na)+, m.p.: 240-242° C.

Workup

  1. customquenched with an aqueous saturated solution of ammonium chloride
  2. extractionThe product is extracted twice with ethyl acetate
  3. customthe combined organic phases are dried on Na2SO4
  4. filtrationfiltrated
  5. customthe solvent is evaporated
  6. customAfter purification by flash chromatography on silica gel with hexanes and ethyl acetate as eluents

Sources & evidence

ORD record
ord-2042812cf56f46dab18f4e8b1865964b
Source dataset
uspto-grants-2014_02
Patent number
US08658801B2

Reaction notes

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