Aniline → HCID 23156213, compound

HRID 1890637Notes

Reaction equation

HRID 1890637 reaction equation
[CH2:1]([C:3]1[N:13]([CH2:14][C:15]2[CH:22]=[CH:21][C:18]([CH2:19]O)=[CH:17][CH:16]=2)[C:6]2=[N:7][C:8]([CH3:12])=[CH:9][C:10]([CH3:11])=[C:5]2[N:4]=1)[CH3:2].C(N(CC)CC)C.CS(Cl)(=O)=O.[NH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>ClCCl.C(Cl)(Cl)Cl.O>[CH2:1]([C:3]1[N:13]([CH2:14][C:15]2[CH:22]=[CH:21][C:18]([CH2:19][NH:35][C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)=[CH:17][CH:16]=2)[C:6]2=[N:7][C:8]([CH3:12])=[CH:9][C:10]([CH3:11])=[C:5]2[N:4]=1)[CH3:2]

Participants

8

Reactant 4

HCID 6115AnilineHCID 8471Triethylamine2×HCID 31297Methanesulfonyl chlorideHCID 23156212HCID 23156212, compound

Product 1

HCID 23156213HCID 23156213, compoundYield 40%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6212ChloroformSolvent2×HCID 6344DichloromethaneSolvent

Procedure

Compound 34 (0.300 g, 1.01 mmol) was dissolved in dichloromethane (10 mL), and triethylamine (0.284 mL, 2.03 mmol) and methanesulfonyl chloride (0.118 mL, 1.52 mmol) was added to the solution at 0° C., followed by stirring for 1.5 hours. The reaction mixture was added with water to decompose excess reagent, and diluted with chloroform, then washed with water and saturated brine. The organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. Then, the residue was dissolved in dichloromethane (10 mL), triethylamine (0.283 mL, 2.03 mmol) and aniline (0.277 mL, 3.04 mmol) was added to the solution, followed by stirring at room temperature overnight. The reaction mixture was diluted with chloroform, and washed with water and saturated brine. The organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:3). The desired compound was crystallized from diisopropyl ether to obtain Compound 35 (0.149 g, yield 40%).

Workup

  1. washwashed with water and saturated brine
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. dissolutionThen, the residue was dissolved in dichloromethane (10 mL)
  5. stirringby stirring at room temperature overnight
  6. washwashed with water and saturated brine
  7. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:3)
  10. customThe desired compound was crystallized from diisopropyl ether

Sources & evidence

ORD record
ord-883e08ab6b004b19ba7cd20de78116e9
Source dataset
uspto-grants-2013_08
Patent number
US08507484B2

Reaction notes

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