1H-Indazol-6-amine → HCID 131725925, compound

HRID 2109603Notes

Reaction equation

HRID 2109603 reaction equation
[Cl:1][C:2]1[C:7]([C:8]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([CH:17]([CH3:19])[CH3:18])=[CH:13][CH:12]=2)=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[NH2:20][C:21]1[CH:29]=[C:28]2[C:24]([CH:25]=[N:26][NH:27]2)=[CH:23][CH:22]=1>CN1C(=O)CCC1.C(Cl)Cl>[ClH:1].[NH:27]1[C:28]2[C:24](=[CH:23][CH:22]=[C:21]([NH:20][C:2]3[C:7]([C:8]([NH:10][C:11]4[CH:16]=[CH:15][C:14]([CH:17]([CH3:19])[CH3:18])=[CH:13][CH:12]=4)=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=3)[CH:29]=2)[CH:25]=[N:26]1

Participants

5

Reactant 2

HCID 814231H-Indazol-6-amineHCID 773658HCID 773658, compound

Product 1

HCID 131725925HCID 131725925, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

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-c823ed94f5b44fabbf00a902b81fc741
Source dataset
uspto-grants-2009_04
Patent number
US07514564B2

Reaction notes

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