HCID 10296324, compound → HCID 21959454, compound

HRID 2214230Notes

Reaction equation

HRID 2214230 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:29])[C:13]2[CH:18]=[CH:17][CH:16]=[N:15][C:14]=2[NH:19][C:20]2[CH:28]=[C:27]3[C:23]([CH:24]=[N:25][NH:26]3)=[CH:22][CH:21]=2)=[CH:7][C:6]=1[N+:30]([O-])=O)([CH3:4])([CH3:3])[CH3:2]>CCO>[NH2:30][C:6]1[CH:7]=[C:8]([NH:11][C:12](=[O:29])[C:13]2[CH:18]=[CH:17][CH:16]=[N:15][C:14]=2[NH:19][C:20]2[CH:28]=[C:27]3[C:23]([CH:24]=[N:25][NH:26]3)=[CH:22][CH:21]=2)[CH:9]=[CH:10][C:5]=1[C:1]([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 1

HCID 10296324HCID 10296324, compound

Product 1

HCID 21959454HCID 21959454, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The title compound was prepared from N-(4-tert-butyl-3-nitro-phenyl)-2-(1H-indazol-6-ylamino)-nicotinamide by dissolving in EtOH (20 ml) and adding Sn(II)Cl2 (12.58 g) and stirred at RT for 5 h and at 0 C. overnight. The mix was warmed to RT and quenched by pouring onto ice, neutralized with NaHCO3 and basified with 6N NAOH. An emulsion formed upon addition of EtOAc which was filtered through Celite and the aqueous layer was extracted with EtOAc. The combined organic layers were washed with H2O, brine and dried over MgSO4 then purified by flash chromatography (3–5% MeOH to afford the product as a orange-yellow solid.

Workup

  1. customovernight
  2. temperatureThe mix was warmed to RT
  3. customquenched
  4. additionby pouring onto ice
  5. customAn emulsion formed upon addition of EtOAc which
  6. filtrationwas filtered through Celite
  7. extractionthe aqueous layer was extracted with EtOAc
  8. washThe combined organic layers were washed with H2O, brine
  9. dry with materialdried over MgSO4
  10. customthen purified by flash chromatography (3–5% MeOH

Sources & evidence

ORD record
ord-55819db3d49b4a3e8b9eae914394255d
Source dataset
uspto-grants-2006_09
Patent number
US07105682B2

Reaction notes

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