Sodium Hydroxide → HCID 178488064, compound

HRID 2064616Notes

Reaction equation

HRID 2064616 reaction equation
N1C=CC=C(CNC(C2C=CC3NC(C4C(C(=O)NC(C)C)=CNN=4)=NC=3C=2)=O)C=1.[NH2:31][C:32]1[CH:37]=[C:36]([O:38][CH3:39])[CH:35]=[CH:34][C:33]=1[NH:40][C:41]([C:43]1[C:47]([N+:48]([O-:50])=[O:49])=[CH:46][NH:45][N:44]=1)=O.[OH-].[Na+]>O>[CH3:39][O:38][C:36]1[CH:35]=[CH:34][C:33]2[NH:40][C:41]([C:43]3[C:47]([N+:48]([O-:50])=[O:49])=[CH:46][NH:45][N:44]=3)=[N:31][C:32]=2[CH:37]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 178457736HCID 178457736, compoundHCID 1784923544-nitro-1H-pyrazole-3-carboxylic acid (2-amino-4-methoxy-phenyl)-amide

Product 1

HCID 178488064HCID 178488064, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

By proceeding in a manner similar to Example 252(a) above but (i) using 4-nitro-1H-pyrazole-3-carboxylic acid (2-amino-4-methoxy-phenyl)-amide [410 mg, Reference Example 36(d)] and heating at 120° C. for 5 minutes, (ii) pouring the reaction mixture into water, adjusting to pH14 with 2N sodium hydroxide and filtering, and (iii) adjusting the pH of the filtrate to 6 with 2N hydrochloric acid and collecting the precipitate by filtration, there was prepared 5-methoxy-2-(4-nitro-1H-pyrazol-3-yl)-1H-benzoimidazole (327 mg) as a yellow powder. LC-MS (Method H): RT=1.61 minutes, 260.25 (M+H)+, 258.26 (M−H)−.

Workup

  1. filtrationfiltering
  2. customcollecting the precipitate
  3. filtrationby filtration, there
  4. customwas prepared 5-methoxy-2-(4-nitro-1H-pyrazol-3-yl)-1H-benzoimidazole (327 mg) as a yellow powder

Sources & evidence

ORD record
ord-2ad935a523f24853ab519e0b0809cfcd
Source dataset
uspto-grants-2012_10
Patent number
US08288425B2

Reaction notes

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