4-Methoxy-5-methylbenzene-1,2-diamine → HCID 178486785, compound

HRID 2064597Notes

Reaction equation

HRID 2064597 reaction equation
[CH:1]([NH:4][C:5]([C:7]1[C:8]([CH:12]=O)=[N:9][NH:10][CH:11]=1)=[O:6])([CH3:3])[CH3:2].[CH3:14][O:15][C:16]1[CH:17]=[C:18]([NH2:24])[C:19]([NH2:23])=[CH:20][C:21]=1[CH3:22]>ClCCl.CO>[CH:1]([NH:4][C:5]([C:7]1[C:8]([C:12]2[NH:23][C:19]3[CH:20]=[C:21]([CH3:22])[C:16]([O:15][CH3:14])=[CH:17][C:18]=3[N:24]=2)=[N:9][NH:10][CH:11]=1)=[O:6])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 224780914-Methoxy-5-methylbenzene-1,2-diamineHCID 178457737HCID 178457737, compound

Product 1

HCID 178486785HCID 178486785, compound

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

By proceeding in a manner similar to Example 235(a) above but using 3-formyl-pyrazole-4-carboxylic acid-isopropylamide [198 mg, Reference Example 60)] and 4-methoxy-5-methyl-benzene-1,2-diamine [166 mg, Reference Example 29(b)] and subjecting the reaction product to flash chromatography on silica eluting with dichloromethane/methanol (95:5) followed by recrystallisation from a mixture of ethyl acetate and n-pentane there was prepared 3-(5-methoxy-6-methyl-1H-benzoimidazol-2-yl)-1H-pyrazole-4-carboxylic acid isopropylamide (145 mg) as a white solid. LC-MS (Method H): RT=2.09 minutes, 314.27 (M+H)+, 312.29 (M−H)−.

Workup

  1. customfollowed by recrystallisation from a mixture of ethyl acetate and n-pentane
  2. customthere was prepared 3-(5-methoxy-6-methyl-1H-benzoimidazol-2-yl)-1H-pyrazole-4-carboxylic acid isopropylamide (145 mg) as a white solid

Sources & evidence

ORD record
ord-2bd688128e414468a11aca5d1ddc9453
Source dataset
uspto-grants-2012_10
Patent number
US08288425B2

Reaction notes

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