Methylamine → 6-{[2-(3-chloro-pyridin-2-yl)-5-trifluoromethyl-2H-pyrazole-3-carbonyl]-amino}-quinoline-5-carboxylic acid methylamide

HRID 245648Notes

Reaction equation

HRID 245648 reaction equation
[Cl:1][C:2]1[C:3]([N:8]2[C:12]([C:13]3[O:26][C:25](=[O:27])[C:24]4[C:23]5[C:18](=[N:19][CH:20]=[CH:21][CH:22]=5)[CH:17]=[CH:16][C:15]=4[N:14]=3)=[CH:11][C:10]([C:28]([F:31])([F:30])[F:29])=[N:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1.[C:32](#[N:34])C.O.CN>[Cl-].[Na+].O>[CH3:32][NH:34][C:25]([C:24]1[C:23]2[CH:22]=[CH:21][CH:20]=[N:19][C:18]=2[CH:17]=[CH:16][C:15]=1[NH:14][C:13]([C:12]1[N:8]([C:3]2[C:2]([Cl:1])=[CH:7][CH:6]=[CH:5][N:4]=2)[N:9]=[C:10]([C:28]([F:30])([F:31])[F:29])[CH:11]=1)=[O:26])=[O:27]

Participants

5

Reactant 3

HCID 6329MethylamineHCID 18373917Acetonitrile--water (1/1)HCID 579901052-[2-(3-chloro-pyridin-2-yl)-5-trifluoromethyl-2H-pyrazol-3-yl]-3-oxa-1,8-diaza-phenanthren-4-one

Product 1

HCID 579900956-{[2-(3-chloro-pyridin-2-yl)-5-trifluoromethyl-2H-pyrazole-3-carbonyl]-amino}-quinoline-5-carboxylic acid methylamideYield 76%

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Procedure

To a suspension of 150 mg (0.30 mmol) of the above 2-[2-(3-chloro-pyridin-2-yl)-5-trifluoromethyl-2H-pyrazol-3-yl]-3-oxa-1,8-diaza-phenanthren-4-one in 6 mL of a mixture acetonitrile: H2O 4:1 (v/v) is added 79 μL (0.91 mmol) of methylamine (solution 40% in water). The reaction mixture is stirred for 6 hours at ambient temperature. Brine is then added to the mixture and the product is extracted with ethyl acetate (3 times). The regrouped organic phases are dried on Na2SO4, filtrated and evaporated. The purification of the residue by flash chromatography (SiO2, heptane/ethyl acetate 1:1) affords 110 mg (76%) of a white solid; LC/MS:475/477 (M+H)+, m.p.: 210-211° C.

Workup

  1. extractionthe product is extracted with ethyl acetate (3 times)
  2. customThe regrouped organic phases are dried on Na2SO4
  3. filtrationfiltrated
  4. customevaporated
  5. customThe purification of the residue by flash chromatography (SiO2, heptane/ethyl acetate 1:1)

Sources & evidence

ORD record
ord-ba13e95b574a4bc089d41d07685b182f
Source dataset
uspto-grants-2014_02
Patent number
US08658801B2

Reaction notes

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