4,5-Dimethyl-1,2-phenylenediamine → HCID 178422286, compound

HRID 2064598Notes

Reaction equation

HRID 2064598 reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([NH2:9])=[C:4]([NH2:10])[CH:3]=1.[O:11]1[CH2:16][CH2:15][CH:14]([NH:17][C:18]([C:20]2[C:21]([CH:25]=O)=[N:22][NH:23][CH:24]=2)=[O:19])[CH2:13][CH2:12]1>>[O:11]1[CH2:16][CH2:15][CH:14]([NH:17][C:18]([C:20]2[C:21]([C:25]3[NH:10][C:4]4[CH:3]=[C:2]([CH3:1])[C:7]([CH3:8])=[CH:6][C:5]=4[N:9]=3)=[N:22][NH:23][CH:24]=2)=[O:19])[CH2:13][CH2:12]1

Participants

3

Reactant 2

HCID 766354,5-Dimethyl-1,2-phenylenediamineHCID 178520058HCID 178520058, compound

Product 1

HCID 178422286HCID 178422286, compound

Procedure

By proceeding in a manner similar to Example 235(i) above but using 4,5-dimethyl-1,2-phenylenediamine and 3-formyl-1H-pyrazole-4-carboxylic acid (tetrahydro-pyran-4-yl)-amide [Reference Example 6(p)] and recrystallising the reaction product from methanol there was prepared 3-(5,6-dimethyl-1H-benzoimidazol-2-yl)-1H-pyrazole-4-carboxylic acid (tetrahydro-pyran-4-yl)-amide (228 mg) as a white solid. LC-MS (METHOD R): RT=9.40 minutes, 360 (M+H)+.

Workup

  1. customrecrystallising the reaction product from methanol
  2. customthere was prepared 3-(5,6-dimethyl-1H-benzoimidazol-2-yl)-1H-pyrazole-4-carboxylic acid (tetrahydro-pyran-4-yl)-amide (228 mg) as a white solid

Sources & evidence

ORD record
ord-b96579b87fb64d54aa2435f03e529456
Source dataset
uspto-grants-2012_10
Patent number
US08288425B2

Reaction notes

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