Pyridine → 3-dimethylamino-N-(5-nitro-1H-indazol-3-yl)-benzamide

HRID 1678226Notes

Reaction equation

HRID 1678226 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][N:8]=[C:7]2[NH2:13])([O-:3])=[O:2].N1C=CC=CC=1.[CH3:20][N:21]([CH3:31])[C:22]1[CH:23]=[C:24]([CH:28]=[CH:29][CH:30]=1)[C:25](Cl)=[O:26]>>[CH3:20][N:21]([CH3:31])[C:22]1[CH:23]=[C:24]([CH:28]=[CH:29][CH:30]=1)[C:25]([NH:13][C:7]1[C:6]2[C:10](=[CH:11][CH:12]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[NH:9][N:8]=1)=[O:26]

Participants

4

Reactant 3

HCID 1049PyridineHCID 31366553-Amino-5-nitroindazoleHCID 70103423-Dimethylaminobenzoyl chloride

Product 1

HCID 590241303-dimethylamino-N-(5-nitro-1H-indazol-3-yl)-benzamide

Procedure

To a solution of 5-nitro-1H-indazol-3-ylamine in pyridine (Ryan Scientific, 0.150 g, 0.838 mmol) cooled to about 0° C. in an ice bath, was added 3-dimethylamino-benzoyl chloride (0.154 g, 0.838 mmol). The reaction mixture was stirred as it warmed to ambient temperature. After about 1 hour it was poured into crushed ice, then extracted with EtOAc (10 mL). The organic solvent portion was washed with a 1M aqueous HCl solution, then concentrated and dried under reduced pressure. The residue was further purified via preparative RP-HPLC (Rainin C18, 8 mm, 300 Å, 35 cm; 5-100% acetonitrile/0.1 M ammonium acetate over 20 min, 100% acetonitrile hold 10 minutes, 21 mL/min) to obtain 3-dimethylamino-N-(5-nitro-1H-indazol-3-yl)-benzamide as a white solid (0.002 g, 0.006 mmol); RP-HPLC (Table 1, Method e) Rt 1.95 min; m/z: (M+H)+ 326.4.

Workup

  1. additionAfter about 1 hour it was poured
  2. custominto crushed ice
  3. extractionextracted with EtOAc (10 mL)
  4. washThe organic solvent portion was washed with a 1M aqueous HCl solution
  5. concentrationconcentrated
  6. customdried under reduced pressure
  7. customThe residue was further purified via preparative RP-HPLC (Rainin C18, 8 mm, 300 Å, 35 cm; 5-100% acetonitrile/0.1 M ammonium acetate over 20 min, 100% acetonitrile hold 10 minutes, 21 mL/min)

Sources & evidence

ORD record
ord-f97d71f40222445b97351ed6b9d4b4ec
Source dataset
uspto-grants-2011_08
Patent number
US08008481B2

Reaction notes

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