Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → HCID 67763089, compound

HRID 2260120Notes

Reaction equation

HRID 2260120 reaction equation
CC1(C)[O:6][C@H:5]([CH2:7][N:8]2[C:12]3=[CH:13][C:14]4[N:15]=[C:16]([C:21]5[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[C:23]([F:29])[CH:22]=5)[CH:17]=[N:18][C:19]=4[CH:20]=[C:11]3[CH:10]=[N:9]2)[CH2:4][O:3]1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>CC(C)=O>[OH:3][CH2:4][C@H:5]([OH:6])[CH2:7][N:8]1[C:12]2=[CH:13][C:14]3[N:15]=[C:16]([C:21]4[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[C:23]([F:29])[CH:22]=4)[CH:17]=[N:18][C:19]=3[CH:20]=[C:11]2[CH:10]=[N:9]1.[OH:3][CH2:4][C@H:5]([OH:6])[CH2:7][N:8]1[CH:12]=[C:11]2[C:10]([CH:13]=[C:14]3[C:19](=[CH:20]2)[N:18]=[CH:17][C:16]([C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[C:23]([F:29])[CH:22]=2)=[N:15]3)=[N:9]1

Participants

5

Reactant 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 57256612HCID 57256612, compound

Product 2

HCID 67763089HCID 67763089, compoundHCID 67763090HCID 67763090, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 0.24 g of 1-[(4R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl]-7-(3-fluoro-4-methoxyphenyl)-1H-pyrazolo[3,4-g]quinoxaline (0.05 g) of pyridinium p-toluenesulfonate and 20 ml of aqueous acetone (1:4H2O:acetone) is heated to reflux overnight. The acetone is then removed in vacuo and the residue mixed with ether, filtered and the yellow solid is treated with saturated NaHCO3, filtered, washed with water and air dried. This is recrystallized from ethylacetate, filtered and dried overnight. This is then recrystallized from CHCl3 and the resultant product purified by column chromatography using 3% MeOH in methylene chloride to obtain 1-[(2R)-1,2-dihydroxyprop-3-yl)-7-(3-fluoro-4-methoxyphenyl)-1H-pyrazolo-[3,4-g]quinoxaline (m.p. 228°-234° C.) and 2-[(2R)-1,2-dihydroxyprop-3-yl)-7-(3-fluoro-4-methoxyphenyl)-2H-pyrazolo-[3,4-g]quinoxaline.

Workup

  1. temperatureis heated
  2. temperatureto reflux overnight
  3. customThe acetone is then removed in vacuo
  4. additionthe residue mixed with ether
  5. filtrationfiltered
  6. additionthe yellow solid is treated with saturated NaHCO3
  7. filtrationfiltered
  8. washwashed with water and air
  9. customdried
  10. customThis is recrystallized from ethylacetate
  11. filtrationfiltered
  12. customdried overnight
  13. customThis is then recrystallized from CHCl3
  14. customthe resultant product purified by column chromatography

Sources & evidence

ORD record
ord-55222b3a11094127be24d898c78446b5
Source dataset
uspto-grants-1995_12
Patent number
US05476851

Reaction notes

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