2-Methylbenzenesulfonic acid → HCID 57682569, compound

HRID 494144Notes

Reaction equation

HRID 494144 reaction equation
[NH2:1][C:2]1[C:7]2[N:8]3[CH2:16][CH2:15][N:14]([CH3:17])[C:13](=[O:18])[C:9]3=[C:10]([O:11]C)[C:6]=2[C:5](=[O:19])[N:4]([CH2:20][C:21]2[CH:26]=[CH:25][C:24]([F:27])=[C:23]([Cl:28])[CH:22]=2)[N:3]=1.[CH3:29][C:30](=O)[CH2:31][CH2:32][C:33](=O)[CH3:34].C1(C)C(S(O)(=O)=O)=CC=CC=1>C1(C)C=CC=CC=1>[Cl:28][C:23]1[CH:22]=[C:21]([CH:26]=[CH:25][C:24]=1[F:27])[CH2:20][N:4]1[C:5](=[O:19])[C:6]2[C:10]([OH:11])=[C:9]3[C:13](=[O:18])[N:14]([CH3:17])[CH2:15][CH2:16][N:8]3[C:7]=2[C:2]([N:1]2[C:33]([CH3:34])=[CH:32][CH:31]=[C:30]2[CH3:29])=[N:3]1

Participants

5

Reactant 3

HCID 69252-Methylbenzenesulfonic acidHCID 80352,5-HexanedioneHCID 68868086HCID 68868086, compound

Product 1

HCID 57682569HCID 57682569, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 4-amino-2-(3-chloro-4-fluorobenzyl)-10-methoxy-8-methyl-7,8-dihydropyrazino[1′,2′:1,5]pyrrolo[2,3-d]pyridazine-1,9(2H,6H)-dione (100 mg, 246 μmol), hexan-2,5-dione (34 mg, 296 μmol), and toluenesulfonic acid (catalytic amount) in toluene (2 mL) was heated in a sealed tube in an oil bath at 120° C. for one hour. The product mixture was concentrated under vacuum. The residue was partitioned between dichloromethane and aqueous sodium bicarbonate. The organic extract was washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum. The residue was subjected to column chromatography on silica gel eluting with a 0-30% methanol in ethyl acetate gradient. Collection and concentration of appropriate fractions provided the title compound.

Workup

  1. concentrationThe product mixture was concentrated under vacuum
  2. customThe residue was partitioned between dichloromethane and aqueous sodium bicarbonate
  3. extractionThe organic extract
  4. washwas washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum
  8. customCollection and concentration of appropriate fractions

Sources & evidence

ORD record
ord-21c42b7b3ad54ea68243eebbb2d1c79e
Source dataset
uspto-grants-2009_05
Patent number
US07538112B2

Reaction notes

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