HCID 178490812, compound → 1-(4-methoxy-benzyl)-3-(5-morpholin-4-ylmethyl-1H-benzimidazol-2-yl)-1H-pyrazol-4-ylamine

HRID 1012136Notes

Reaction equation

HRID 1012136 reaction equation
[CH3:1][O:2][C:3]1[CH:33]=[CH:32][C:6]([CH2:7][N:8]2[CH:12]=[C:11]([N+:13]([O-])=O)[C:10]([C:16]3[NH:20][C:19]4[CH:21]=[CH:22][C:23]([CH2:25][N:26]5[CH2:31][CH2:30][O:29][CH2:28][CH2:27]5)=[CH:24][C:18]=4[N:17]=3)=[N:9]2)=[CH:5][CH:4]=1>[Fe].O1CCOCC1.O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][N:8]2[CH:12]=[C:11]([NH2:13])[C:10]([C:16]3[NH:20][C:19]4[CH:21]=[CH:22][C:23]([CH2:25][N:26]5[CH2:27][CH2:28][O:29][CH2:30][CH2:31]5)=[CH:24][C:18]=4[N:17]=3)=[N:9]2)=[CH:32][CH:33]=1

Participants

4

Reactant 1

HCID 178490812HCID 178490812, compound

Product 1

HCID 1784908051-(4-methoxy-benzyl)-3-(5-morpholin-4-ylmethyl-1H-benzimidazol-2-yl)-1H-pyrazol-4-ylamineYield 94%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

To a mixture of 2-[1-(4-methoxy-benzyl)-4-nitro-1H-pyrazol-3-yl]-5-morpholin-4-ylmethyl-1H-benzimidazole (1.6 g, 3.57 mmol), Fe powder (2 g, 35 mmol) and FeSO4.7H2O (0.496 g, 1.78 mmol) was added 1,4-dioxane:water (5:1, 120 ml). The mixture was refluxed for 3 h, filtered through celite, washing with MeOH, and reduced in vacuo azeotroping with toluene. EtOAc (100 ml) was added and insoluble material removed via filtration. The filtrate was reduced in vacuo to give 1-(4-methoxy-benzyl)-3-(5-morpholin-4-ylmethyl-1H-benzimidazol-2-yl)-1H-pyrazol-4-ylamine as a dark brown solid (1.4 g, 94%). (LC/MS: Rt 1.72, [M+H]+ 419).

Workup

  1. temperatureThe mixture was refluxed for 3 h
  2. filtrationfiltered through celite
  3. washwashing with MeOH
  4. customazeotroping with toluene
  5. additionEtOAc (100 ml) was added
  6. custominsoluble material removed via filtration

Sources & evidence

ORD record
ord-c6d5152f62214381bbbf74b67466ee33
Source dataset
uspto-grants-2011_07
Patent number
US07977477B2

Reaction notes

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