Aniline → HCID 86749371, compound

HRID 1441144Notes

Reaction equation

HRID 1441144 reaction equation
[C:1]1([NH2:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([N:10](CC)CC)C.[CH3:15][S:16](Cl)(=[O:18])=[O:17].C(=O)(O)[O-].[Na+]>ClCCl>[CH3:15][S:16]([NH2:10])(=[O:18])=[O:17].[CH3:15][S:16]([NH2:7])(=[O:18])=[O:17].[C:1]1([NH2:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 6115AnilineHCID 8471TriethylamineHCID 31297Methanesulfonyl chloride2×HCID 516892Sodium Bicarbonate

Product 1

HCID 86749371HCID 86749371, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-(7-methyl-2,4-di-1-pyrrolidinyl-7H-pyrrolo- 2,3-d!pyrimidin-6-yl)phenylamine (EXAMPLE 188, 206 mg) in 40 ml of dichloromethane is cooled in an ice-water bath and treated with 0.15 ml of triethylamine followed by 0.05 ml of methanesulfonyl chloride. Three additional portions of methanesulfonyl chloride, 0.02 ml, 0.01 ml and 0.01 ml, are added in sequence over the next hour. The mixture is poured onto water, treated with aqueous saturated sodium bicarbonate and extracted with three portions of dichloromethane. The combined organic extracts are dried and concentrated to give a solid which is combined with previously isolated material (from a 50 mg run) and chromatographed over silica eluting with methanol/chloroform (3/97) to give the desired material which is recrystallized from hot acetonitrile to give the title compound, mp 245-248; NMR 7.49-7.47, 7.31-7.28, 6.42, 3.78-3.69, 3.64, 3.58-3.52, 3.36, 1.97-1.85δ.

Workup

  1. temperatureis cooled in an ice-water bath
  2. additionThe mixture is poured onto water
  3. extractionextracted with three portions of dichloromethane
  4. customThe combined organic extracts are dried
  5. concentrationconcentrated
  6. customto give a solid which
  7. customchromatographed over silica eluting with methanol/chloroform (3/97)

Sources & evidence

ORD record
ord-4a4383738fb54637b70427c23428263e
Source dataset
uspto-grants-1996_03
Patent number
US05502187

Reaction notes

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