Acetic Acid → Diisopropyl Ether

HRID 2243355Notes

Reaction equation

HRID 2243355 reaction equation
[N:1]1([CH2:6][CH2:7][NH:8][C:9]([C:11]2[CH:34]=[CH:33][C:14]3[NH:15][C:16]([C:18]4[C:30]5[C:29]6[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=6)[C:23](=[N:31]O)[C:22]=5[CH:21]=[CH:20][CH:19]=4)=[N:17][C:13]=3[CH:12]=2)=[O:10])[CH2:5][CH2:4][CH2:3][CH2:2]1.[C:35]([OH:38])(=O)[CH3:36].[CH2:39](O)C>O.[Zn]>[CH:35]([O:38][CH:34]([CH3:33])[CH3:11])([CH3:36])[CH3:39].[N:1]1([CH2:6][CH2:7][NH:8][C:9]([C:11]2[CH:34]=[CH:33][C:14]3[NH:15][C:16]([C:18]4[C:30]5[C:29]6[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=6)[CH:23]([NH2:31])[C:22]=5[CH:21]=[CH:20][CH:19]=4)=[N:17][C:13]=3[CH:12]=2)=[O:10])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

7

Reactant 3

HCID 176Acetic AcidHCID 702EthanolHCID 178523404HCID 178523404, compound

Product 2

HCID 7914Diisopropyl EtherHCID 178507133HCID 178507133, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 962WaterSolvent

Procedure

The procedure used in Example 216 is followed. In a 20 ml round-bottomed flask under an argon atmosphere, dissolve 303 mg of 4-{5-[2-(pyrrolidin-1-yl)ethylaminocarbonyl]-1H-benzimidazol-2-yl}-9H -fluoren-9-one oxime (Z,E), obtained in the previous stage, in a mixture of 1.5 ml of ethanol and 1.5 ml of water and 1.5 ml of acetic acid, at room temperature. Add 175 mg of zinc in three stages, and, between each addition, stir for approximately one hour to two hours. Add Celite and filter. The filtrate is concentrated under reduced pressure. 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 by volume) and then formation of a paste with diisopropyl ether, in this way we obtain 257 mg of 4-{5-[2-(pyrrolidin-1-yl)ethylaminocarbonyl]-1H-benzimidazol-2-yl}-9H-fluorene-9(R,S)-amine, in the form of a beige solid, which is used as it is in the following stage, with the following characteristics:

Workup

  1. additionbetween each addition
  2. filtrationAdd Celite and filter
  3. concentrationThe filtrate is concentrated under reduced pressure
  4. customAfter purification by flash chromatography on silica gel (40-63 μm)
  5. washeluting with a mixture of dichloromethane and ammonia as a 7N solution in methanol (9/1 by volume)

Sources & evidence

ORD record
ord-fd86c1a38d654f339e21d14c21ddc6ee
Source dataset
uspto-grants-2010_03
Patent number
US07674795B2

Reaction notes

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