Acetic Acid → HCID 178507136, compound

HRID 2243374Notes

Reaction equation

HRID 2243374 reaction equation
[F:1][C:2]1[C:25]([OH:26])=[CH:24][C:5]2[NH:6][C:7]([C:9]3[C:21]4[C:20]5[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=5)[C:14](=[N:22]O)[C:13]=4[CH:12]=[CH:11][CH:10]=3)=[N:8][C:4]=2[CH:3]=1.C(O)(=O)C>C(O)C.O.[Zn]>[F:1][C:2]1[C:25]([OH:26])=[CH:24][C:5]2[NH:6][C:7]([C:9]3[C:21]4[C:20]5[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=5)[CH:14]([NH2:22])[C:13]=4[CH:12]=[CH:11][CH:10]=3)=[N:8][C:4]=2[CH:3]=1

Participants

6

Reactant 2

HCID 176Acetic AcidHCID 178526307HCID 178526307, compound

Product 1

HCID 178507136HCID 178507136, compound

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

The procedure used in stage 4 of Example 216 is followed. In a 30 ml round-bottomed flask under an argon atmosphere, dissolve 667 mg of equimolecular mixture of 4-(5-fluoro-6-hydroxy-1H-benzimidazol-2-yl)-9H-fluoren-9-one oxime (Z,E), obtained in the previous stage, in a mixture of 3.5 ml of ethanol and 3.5 ml of water and 3.5 ml of acetic acid; at room temperature, add 500 mg of zinc in three stages. Between each addition, stir for approximately one hour to two hours. After purification by flash chromatography on silica gel (40-63 μm), eluting with a mixture of dichloromethane and ammonia as a 7N solution in methanol (9/1 then 85/15 by volume), in this way we obtain 456 mg of 4-(5-fluoro-6-hydroxy-1H-benzimidazol-2-yl)-9H-fluorene-9(R,S)-amine, in the form of a beige powder, which is used as it is in the following stage, with the following characteristics:

Workup

  1. additionBetween each addition
  2. customAfter purification by flash chromatography on silica gel (40-63 μm)
  3. washeluting with a mixture of dichloromethane and ammonia as a 7N solution in methanol (9/1

Sources & evidence

ORD record
ord-530175ff4ce64d2b8aabe2e8ceba64a6
Source dataset
uspto-grants-2010_03
Patent number
US07674795B2

Reaction notes

Loading…