N-methyl-2-pyrrolidone → HCID 69137510, compound

HRID 2214192Notes

Reaction equation

HRID 2214192 reaction equation
[Cl:1]C1C(C(N[C:11]2[CH:16]=[CH:15][C:14]([CH:17]([CH3:19])[CH3:18])=[CH:13][CH:12]=2)=O)=CC=CN=1.NC1C=C2C(C=NN2)=CC=1.C[N:31]1[C:35](=[O:36])CCC1>C(Cl)Cl>[ClH:1].[CH3:19][CH:17]([C:14]1[CH:13]=[CH:12][C:11]([C:35]([NH2:31])=[O:36])=[CH:16][CH:15]=1)[CH3:18]

Participants

5

Reactant 3

HCID 13387N-methyl-2-pyrrolidoneHCID 814231H-Indazol-6-amineHCID 773658HCID 773658, compound

Product 1

HCID 69137510HCID 69137510, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of (2-chloro(3-pyridyl))-N-(4-isopropylphenyl)carboxamide (1.5 g, Step A) and 6-aminoindazole (880 mg) was heated at 160° C. in NMP for 3 h. The reaction was cooled and diluted with CH2Cl2 and washed with water twice, followed by brine. The organic layer was dried with Na2SO4 and evaporated under reduced pressure. The residue was purified by column chromatography with 35% EtOAc/Hexane and further mixed with MeOH and 1 N HCl/Et2O (3 ml). The solution was evaporated to furnish the titled compound. MS (ES+): 372 (M+H)+; (ES−): 371 (M−H). Calc'd. for C22H21N5O—371.2.

Workup

  1. temperatureThe reaction was cooled
  2. washwashed with water twice
  3. dry with materialThe organic layer was dried with Na2SO4
  4. customevaporated under reduced pressure
  5. customThe residue was purified by column chromatography with 35% EtOAc/Hexane
  6. additionfurther mixed with MeOH and 1 N HCl/Et2O (3 ml)
  7. customThe solution was evaporated

Sources & evidence

ORD record
ord-726ff883b07043f7b433d8d1fab0eb2b
Source dataset
uspto-grants-2006_09
Patent number
US07105682B2

Reaction notes

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