Ethyl Acetate → HCID 178494021, compound

HRID 1191252Notes

Reaction equation

HRID 1191252 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:13]=[C:12]([O:14][CH3:15])[C:11]([N+:16]([O-])=O)=[C:10]([NH:19][C:20]([C:22]2[N:23]([CH3:32])[N:24]=[C:25]([C:28]([CH3:31])([CH3:30])[CH3:29])[C:26]=2[Cl:27])=O)[CH:9]=1.CCOC(C)=O>CC(O)=O.CCOCC.[Fe]>[C:28]([C:25]1[C:26]([Cl:27])=[C:22]([C:20]2[NH:16][C:11]3[C:12]([O:14][CH3:15])=[N:13][C:8]([C:3]4[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=4[Cl:1])=[CH:9][C:10]=3[N:19]=2)[N:23]([CH3:32])[N:24]=1)([CH3:31])([CH3:30])[CH3:29]

Participants

6

Reactant 2

HCID 8857Ethyl AcetateHCID 674096383-tert-butyl-4-chloro-N-(6-(2-chlorophenyl)-2-methoxy-3-nitropyridin-4-yl)-1-methyl-1H-pyrazole-5-carboxamide

Product 1

HCID 178494021HCID 178494021, compound

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 5-tert-butyl-4-chloro-2-methyl-2H-pyrazole-3-carboxylic acid [6-(2-chloro-phenyl)-2-methoxy-3-nitro-pyridin-4-yl]-amide (9.10 g, 32.6 mmol, prepared as described in the previous step above) in AcOH (50 mL) was treated with iron powder (6.80 g, 122 mmol) and heated to 100° C. for 3 h. The resulting mixture was cooled to room temperature and treated with EtOAc (100 mL). The resulting mixture was then filtered through a pad of diatomaceous earth and the filtrate was concentrated in vacuo. The residue was purified on silica (0:100-100:0 EtOAc/hexane) to yield a white solid. The solid obtained was dissolved in Et2O (200 mL) with heating and sonication. Hexanes (50 mL) were added and the resulting mixture was concentrated until a precipitate started to form. The solution was left at room temperature overnight and the solid formed was collected by suction filtration to yield 2-(5-tert-butyl-4-chloro-2-methyl-2H-pyrazol-3-yl)-6-(2-chloro-phenyl)-4-methoxy-3H-imidazo[4,5-c]pyridine. 1H-NMR (400 MHz, CD3OD) δ: 7.76-7.58 (m, 1H), 7.49 (m, 2H), 7.39 (m, 2H), 4.16 (s, 3H), 4.04 (s, 3H), 1.44 (s, 9H). Mass Spectrum (LCMS, ESI pos.) Calculated for C21H21N5OCl2: 430.1 (M+H), Measured: 430.2.

Workup

  1. temperatureThe resulting mixture was cooled to room temperature
  2. filtrationThe resulting mixture was then filtered through a pad of diatomaceous earth
  3. concentrationthe filtrate was concentrated in vacuo
  4. customThe residue was purified on silica (0:100-100:0 EtOAc/hexane)
  5. customto yield a white solid
  6. customThe solid obtained
  7. temperaturewith heating
  8. customsonication
  9. concentrationthe resulting mixture was concentrated until a precipitate
  10. customto form
  11. customthe solid formed
  12. filtrationwas collected by suction filtration

Sources & evidence

ORD record
ord-c884071bd0974c12976d2e05a1353f77
Source dataset
uspto-grants-2014_03
Patent number
US08680098B2

Reaction notes

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