HCID 10296324, compound → HCID 21959454, compound

HRID 2109642Notes

Reaction equation

HRID 2109642 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

Conditions

Temperature
0 °C

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

Sources & evidence

ORD record
ord-fde5f0fab103472dac11c581d8989a78
Source dataset
uspto-grants-2009_04
Patent number
US07514564B2

Reaction notes

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