Toluene → HCID 135464264, compound

HRID 456671Notes

Reaction equation

HRID 456671 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]([C:11]2[NH:12][C:13]([C:16]3[C:24]4[C:19](=[CH:20][CH:21]=[C:22]([N+:25]([O-:27])=[O:26])[CH:23]=4)[NH:18][N:17]=3)=[CH:14][CH:15]=2)=[O:10])[CH:5]=[CH:6][CH:7]=1.[C:28]1(C)C=CC=CC=1>CNN.CN1CCCC1=O>[F:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]([C:11]2[NH:12][C:13]([C:16]3[C:24]4[C:19](=[CH:20][CH:21]=[C:22]([N+:25]([O-:27])=[O:26])[CH:23]=4)[N:18]([CH3:28])[N:17]=3)=[CH:14][CH:15]=2)=[O:10])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 1140TolueneHCID 135401118HCID 135401118, compound

Product 1

HCID 135464264HCID 135464264, compound

Reagents, catalysts & solvents 2

HCID 6061MethylhydrazineCatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 5-(2-chloro-5-nitro-benzoyl)-1H-pyrrole-2-carboxylic acid (3-fluoro-phenyl)-amide (250 mg, 0.6 mmol) (Example 47), methyl hydrazine (4 drops), toluene (0.6 mL) and 1-methyl-pyrrolin-2-one (0.2 mL) was heated at 120° C. for 2 hours. The reaction was concentrated, triturated with DCM and hexane to give 55 mg of the titled compound as a yellow solid.

Workup

  1. concentrationThe reaction was concentrated
  2. customtriturated with DCM and hexane

Sources & evidence

ORD record
ord-4eb405362d0c470d8923479e38e75084
Source dataset
uspto-grants-2007_03
Patent number
US07186716B2

Reaction notes

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