Benzoyl chloride, 3-chloro- → 1h-Indazole-1-carboxylic acid,3-[(3-chlorobenzoyl)amino]-5-nitro-,1,1-dimethylethyl ester

HRID 1823910Notes

Reaction equation

HRID 1823910 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([N+:17]([O-:19])=[O:18])=[CH:14][CH:15]=2)[C:10]([NH2:20])=[N:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:21][C:22]1[CH:23]=[C:24]([CH:28]=[CH:29][CH:30]=1)[C:25](Cl)=[O:26]>N1C=CC=CC=1.CCOC(C)=O>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([N+:17]([O-:19])=[O:18])=[CH:14][CH:15]=2)[C:10]([NH:20][C:25](=[O:26])[C:24]2[CH:28]=[CH:29][CH:30]=[C:22]([Cl:21])[CH:23]=2)=[N:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 69252Benzoyl chloride, 3-chloro-HCID 23571039tert-Butyl 3-amino-5-nitro-1H-indazole-1-carboxylate

Product 1

HCID 235710371h-Indazole-1-carboxylic acid,3-[(3-chlorobenzoyl)amino]-5-nitro-,1,1-dimethylethyl esterYield 39%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-Amino-5-nitroindazole-1-carboxylic acid tert-butyl ester (600 mg, 2 mmol) was dissolved in dry pyridine (15 mL) under nitrogen. The solution was cooled on an ice bath and 3-chlorobenzoyl chloride (0.3 mL, 2 mmol) added. After 6 hours, the mixture was diluted with EtOAc, washed with 1M hydrochloric acid solution (×3) and brine then dried over magnesium sulfate and concentrated to a solid. Purification by column chromatography (silica, 7:3 petrol)-EtOAc) afforded the title compound as a solid (300 mg, 39%); 1H NMR (400 MHz, CDCl3) 1.77 (9H, s), 7.52 (1H, t), 7.62 (1H, d), 7.90 (1H, d), 8.07 (1H, m), 8.32 (1H, d), 8.45 (1H, d), 9.22 (1H, brs), 9.32 (1H, s); MS (ES+) m/e=417.

Workup

  1. temperatureThe solution was cooled on an ice bath
  2. washwashed with 1M hydrochloric acid solution (×3) and brine
  3. dry with materialthen dried over magnesium sulfate
  4. concentrationconcentrated to a solid
  5. customPurification by column chromatography (silica, 7:3 petrol)-EtOAc)

Sources & evidence

ORD record
ord-04539b7dc0a84cd39bff50a3fd04d1b6
Source dataset
uspto-grants-2006_05
Patent number
US07041687B2

Reaction notes

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