9-Oxofluorene-4-carboxylic acid → HCID 67358877, compound

HRID 2243327Notes

Reaction equation

HRID 2243327 reaction equation
[NH2:1][C:2]1[C:7]([NH-:8])=[C:6]([F:9])[C:5]([F:10])=[CH:4][CH:3]=1.[O:11]=[C:12]1[C:24]2[CH:23]=[CH:22][CH:21]=[C:20]([C:25](O)=O)[C:19]=2[C:18]2[C:13]1=[CH:14][CH:15]=[CH:16][CH:17]=2.C(=O)([O-])O.[Na+]>C(O)(=O)C.O>[F:9][C:6]1[C:7]2[N:8]=[C:25]([C:20]3[C:19]4[C:18]5[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=5)[C:12](=[O:11])[C:24]=4[CH:23]=[CH:22][CH:21]=3)[NH:1][C:2]=2[CH:3]=[CH:4][C:5]=1[F:10]

Participants

6

Reactant 3

HCID 803619-Oxofluorene-4-carboxylic acidHCID 516892Sodium BicarbonateHCID 86621030HCID 86621030, compound

Product 1

HCID 67358877HCID 67358877, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Conditions

Temperature
115 °C

Procedure

The procedure used in Example 68 is followed. In a 100 ml round-bottomed flask under an argon atmosphere, heat, at 115° C. for 6 hours, a suspension of 1.7 g of (6-amino-2,3-difluorophenyl)amide of 9-oxo-9H-fluorene-4-carboxylic acid, obtained in the previous stage, in 35 ml of acetic acid. After cooling, bring to dryness under reduced pressure. Take the residue up in water and bring to pH=8 by adding a 10% saturated aqueous solution of sodium hydrogen carbonate, with water. The precipitate that formed is filtered off, washed with water, and rinsed with diisopropyl ether. In this way, we obtain 1.5 g of 4-(4,5-difluoro-1H-benzimidazol-2-yl)-9H-fluoren-9-one, in the form of an orange powder, which is used as it is in the following stage, with the following characteristics:

Workup

  1. temperatureAfter cooling
  2. customThe precipitate that formed
  3. filtrationis filtered off
  4. washwashed with water
  5. washrinsed with diisopropyl ether

Sources & evidence

ORD record
ord-ff16e9ff9fa2493c815b1fd932601354
Source dataset
uspto-grants-2010_03
Patent number
US07674795B2

Reaction notes

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