Acetic Acid → HCID 178509505, compound

HRID 2243332Notes

Reaction equation

HRID 2243332 reaction equation
[C:1]([C:3]1[CH:26]=[CH:25][C:6]2[NH:7][C:8]([C:10]3[C:22]4[C:21]5[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=5)[C:15](=[N:23]O)[C:14]=4[CH:13]=[CH:12][CH:11]=3)=[N:9][C:5]=2[CH:4]=1)#[N:2].C(O)(=O)C>C(O)C.O.[Zn]>[C:1]([C:3]1[CH:26]=[CH:25][C:6]2[NH:7][C:8]([C:10]3[C:22]4[C:21]5[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=5)[CH:15]([NH2:23])[C:14]=4[CH:13]=[CH:12][CH:11]=3)=[N:9][C:5]=2[CH:4]=1)#[N:2]

Participants

6

Reactant 2

HCID 176Acetic AcidHCID 178509506HCID 178509506, compound

Product 1

HCID 178509505HCID 178509505, compound

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

In a 100 ml round-bottomed flask under an argon atmosphere, dissolve 1.58 g of an equimolar mixture of 4-(5-cyano-1H-benzimidazol-2-yl)-9H-fluoren-9-one oxime (Z,E), obtained in the previous stage, in a mixture of 10 ml of ethanol and 10 ml of water and 10 ml of acetic acid, at room temperature, add 1.2 g of zinc in three stages, and stir for approximately one hour to two hours between each addition. Add Celite and filter. The filtrate is concentrated under pressure. The crude product is purified by flash chromatography on silica gel (40-63 μm), eluting with a mixture of dichloromethane and methanol (9/1 by volume) and then a mixture of dichloromethane and ammonia as a 7N solution in methanol (95/5 by volume). In this way, we obtain 1.4 g of 4-(5-cyano-1H-benzimidazol-2-yl)-9H-fluorene-9(R,S)-amine, in the form of a white powder, which is used as it is in the following stage.

Workup

  1. filtrationAdd Celite and filter
  2. concentrationThe filtrate is concentrated under pressure
  3. customThe crude product is purified by flash chromatography on silica gel (40-63 μm)
  4. washeluting with a mixture of dichloromethane and methanol (9/1 by volume)
  5. additiona mixture of dichloromethane and ammonia as a 7N solution in methanol (95/5 by volume)

Sources & evidence

ORD record
ord-5385e7bc3e5e42e4969686f2205db517
Source dataset
uspto-grants-2010_03
Patent number
US07674795B2

Reaction notes

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