Acetic Acid → HCID 178486891, compound

HRID 2243372Notes

Reaction equation

HRID 2243372 reaction equation
[F:1][C:2]1[C:25]([O:26][CH3:27])=[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.O.C(O)(=O)C>C(O)C.[Zn]>[F:1][C:2]1[C:25]([O:26][CH3:27])=[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 3

HCID 176Acetic AcidHCID 962WaterHCID 178486892HCID 178486892, compound

Product 1

HCID 178486891HCID 178486891, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 702EthanolSolvent

Procedure

The procedure used in stage 4 of Example 216 is followed. In a 30 ml round-bottomed flask under an argon atmosphere, dissolve 140 mg of equimolecular mixture of 4-(5-fluoro-6-methoxy-1H-benzimidazol-2-yl)-9H-fluoren-9-one oxime (Z,E), obtained in the previous stage, in a mixture of 0.7 ml of ethanol, 0.7 ml of water and 0.7 ml of acetic acid. At room temperature, add 100 mg of zinc, in three stages, and, 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 (95/5 by volume), in this way we obtain 127 mg of 4-(5-fluoro-6-methoxy-1H -benzimidazol-2-yl)-9H-fluorene-9(R,S)-amine, in the form of a beige resin which is used as it is in the following stage, with the following characteristics:

Workup

  1. additionin three stages, and, between 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 (95/5 by volume), in this way we

Sources & evidence

ORD record
ord-ced8ebabaf154be5aee417a6b13e2240
Source dataset
uspto-grants-2010_03
Patent number
US07674795B2

Reaction notes

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