9H-Fluoren-9-one, 2,7-diamino- → HCID 10437549, compound

HRID 2120923Notes

Reaction equation

HRID 2120923 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([S:9](Cl)(=[O:11])=[O:10])[CH:6]=[CH:7][CH:8]=1.[NH2:13][C:14]1[CH:26]=[CH:25][C:24]2[C:23]3[C:18](=[CH:19][C:20]([NH2:27])=[CH:21][CH:22]=3)[C:17](=[O:28])[C:16]=2[CH:15]=1>C1COCC1.N1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([S:9]([NH:13][C:14]2[CH:26]=[CH:25][C:24]3[C:23]4[C:18](=[CH:19][C:20]([NH:27][S:9]([C:5]5[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=5)(=[O:11])=[O:10])=[CH:21][CH:22]=4)[C:17](=[O:28])[C:16]=3[CH:15]=2)(=[O:11])=[O:10])[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 972389H-Fluoren-9-one, 2,7-diamino-HCID 27375043-Methoxybenzenesulfonyl chloride

Product 1

HCID 10437549HCID 10437549, compoundYield 55.4%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

3-Methoxybenzenesulfonyl chloride (4.75 g, 23.0 mmol) in THF (40 mL) was treated with the product from Example 16A (5.05 g, 24 mmol) in THF (60 mL) and pyridine (60 mL) over 10 minutes. After an additional 30 minutes, the mixture was quenched with a mixture of 1.0M (pH 6) aqueous potassium phosphate buffer (30 mL) and brine (20 mL). The aqueous phase was separated and extracted with diethyl ether. The organic phases were combined, washed 1.0M (pH 6) aqueous potassium phosphate buffer (10 mL) and brine (10 mL), and the aqueous phase was extracted with diethyl ether. All the organic phases were combined, dried (Na2SO4), concentrated, and the filtrate concentrated under reduced pressure. The residue was purified by flash chromatography (ethyl acetate/CH2Cl2). The appropriate fractions were concentrated, dissolved in a small quantity of hot methanol and triturated with diethyl ether. The resulting precipitate was collected by filtration and washed with (10% methanol/diethyl ether) to provide the title compound as an orange powder (3.51 g). 1H HNMR (DMSO-d6) δ 10.55 (bs, 2H), 7.53 (d, J=8.5 Hz, 2H), 7.47 (t, J=8.0 Hz, 2H), 7.33 (d, J=7.6 Hz, 2H), 7.28-7.24 (m, 6H), 7.18 (dd, J=8.5, 2.1, 2H), 3.77 (s, 6H); MS calculated for (M+H): 550.0868; observed: 550.0848; IR 3232, 2971, 1719, 1599, 1466, 1256, 1155.

Workup

  1. customthe mixture was quenched with a mixture of 1.0M (pH 6) aqueous potassium phosphate buffer (30 mL) and brine (20 mL)
  2. customThe aqueous phase was separated
  3. extractionextracted with diethyl ether
  4. washwashed 1.0M (pH 6) aqueous potassium phosphate buffer (10 mL) and brine (10 mL)
  5. extractionthe aqueous phase was extracted with diethyl ether
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated
  8. concentrationthe filtrate concentrated under reduced pressure
  9. customThe residue was purified by flash chromatography (ethyl acetate/CH2Cl2)
  10. concentrationThe appropriate fractions were concentrated
  11. dissolutiondissolved in a small quantity of hot methanol
  12. customtriturated with diethyl ether
  13. filtrationThe resulting precipitate was collected by filtration
  14. washwashed with (10% methanol/diethyl ether)

Sources & evidence

ORD record
ord-66aacaee1dc2425abae4a78881be2bee
Source dataset
uspto-grants-2004_02
Patent number
US06693136B1

Reaction notes

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