Methanesulfonyl chloride → HCID 20703632, compound

HRID 429291Notes

Reaction equation

HRID 429291 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH:3]1[CH:8]([NH:10][C:11]1[N:16]=[C:15]([N:17]2[C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=3[N:19]=[CH:18]2)[CH:14]=[CH:13][N:12]=1)[CH3:9].[CH3:26][S:27](Cl)(=[O:29])=[O:28].OS([O-])(=O)=O.[Na+]>C(Cl)Cl.N1C=CC=CC=1>[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([S:27]([CH3:26])(=[O:29])=[O:28])[CH2:4][CH:3]1[CH:8]([NH:10][C:11]1[N:16]=[C:15]([N:17]2[C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=3[N:19]=[CH:18]2)[CH:14]=[CH:13][N:12]=1)[CH3:9]

Participants

6

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 516919Sodium BisulfateHCID 20703633HCID 20703633, compound

Product 1

HCID 20703632HCID 20703632, compoundYield 13.5%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

To a 0° C. solution of 2-[1-(1-methylpiperazine-2-yl)-ethylamino]-4[-benzimidazol-1-yl]-pyrimidine (EXAMPLE 20; 6 mg) in 1 mL of CH2Cl2 and 0.5 mL of pyridine was added methanesulfonyl chloride (2.5 mg). The mixture was allowed to warm to room temperature and stirred overnight, then poured into 10 mL of 1M NaHSO4, extracted with 2×5 mL of CH2Cl2, basified (pH>10) with 5N NaOH, and extracted with 5×5 mL of EtOAc. The combined EtOAc extracts were washed with 5 mL of brine, dried over Na2SO4 and concentrated. The residue was purified by preparative thin-layer chromatography, eluting with 9:1 CH2Cl2—2M NH3 in MeOH to provide 1.0 mg of the title compound. Mass spectrum (ESI) 416.3 (M+1).

Workup

  1. extractionextracted with 2×5 mL of CH2Cl2
  2. extractionextracted with 5×5 mL of EtOAc
  3. washThe combined EtOAc extracts were washed with 5 mL of brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified by preparative thin-layer chromatography
  7. washeluting with 9:1 CH2Cl2—2M NH3 in MeOH

Sources & evidence

ORD record
ord-b78107ca786a4360b50bbdee5206c913
Source dataset
uspto-grants-2001_11
Patent number
US06316444B1

Reaction notes

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