HCID 131730050, compound → HCID 131730049, compound

HRID 2070343Notes

Reaction equation

HRID 2070343 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[N:13]([CH3:14])[C:12]3[CH:15]=[CH:16][C:17]([O:19][C:20]4[CH:25]=[CH:24][N:23]=[C:22]([C:26]([NH:28][CH3:29])=[O:27])[CH:21]=4)=[CH:18][C:11]=3[N:10]=2)=[CH:4][C:3]=1[N+:30]([O-])=O>C(O)(=O)C.[Fe]>[NH2:30][C:3]1[CH:4]=[C:5]([NH:8][C:9]2[N:13]([CH3:14])[C:12]3[CH:15]=[CH:16][C:17]([O:19][C:20]4[CH:25]=[CH:24][N:23]=[C:22]([C:26]([NH:28][CH3:29])=[O:27])[CH:21]=4)=[CH:18][C:11]=3[N:10]=2)[CH:6]=[CH:7][C:2]=1[Cl:1]

Participants

4

Reactant 1

HCID 131730050HCID 131730050, compound

Product 1

HCID 131730049HCID 131730049, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

To (4-{2-[(4-chloro-3-nitrophenyl)amino]-1-methylbenzimidazol-5-yloxy}-(2-pyridyl))-N-methylcarboxamide in acetic acid was added Fe dust (3 eq) and stirred at ambient temperature for 16 h. The mixture was then filtered and basified with saturated sodium bicarbonate and partitioned between ethyl acetate and water. The organic layer was dried with sodium sulfate and concentrated and passed through a plug of silica to yield (4-{2-[(3-amino-4-chlorophenyl)amino]-1-methylbenzimidazol-5-yloxy}-(2-pyridyl))-N-methylcarboxamide.

Workup

  1. filtrationThe mixture was then filtered
  2. custompartitioned between ethyl acetate and water
  3. dry with materialThe organic layer was dried with sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-f2c6df3002a74457b2f676eb3ffa5043
Source dataset
uspto-grants-2012_10
Patent number
US08299108B2

Reaction notes

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