Dimethylsulphamoyl chloride → 1-[5-(Dimethylaminosulfonylamino)indole-2-carbonyl]-4-[N-methyl-N-(3-(1-methylethylamino)-2-pyridinyl)amino]piperidine

HRID 2293781Notes

Reaction equation

HRID 2293781 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([N:13]1[CH2:18][CH2:17][CH:16]([N:19]([CH3:30])[C:20]3[C:25]([NH:26][CH:27]([CH3:29])[CH3:28])=[CH:24][CH:23]=[CH:22][N:21]=3)[CH2:15][CH2:14]1)=[O:12])=[CH:5]2.[CH3:31][N:32]([CH3:37])[S:33](Cl)(=[O:35])=[O:34]>N1C=CC=CC=1.C(Cl)Cl.Cl>[CH3:31][N:32]([CH3:37])[S:33]([NH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([N:13]1[CH2:18][CH2:17][CH:16]([N:19]([CH3:30])[C:20]3[C:25]([NH:26][CH:27]([CH3:28])[CH3:29])=[CH:24][CH:23]=[CH:22][N:21]=3)[CH2:15][CH2:14]1)=[O:12])=[CH:5]2)(=[O:35])=[O:34]

Participants

6

Reactant 2

HCID 83372Dimethylsulphamoyl chlorideHCID 153920561-[5-aminoindole-2-carbonyl]-4-[N-methyl-N-(3-(1-methylethylamino)-2-pyridinyl)amino]piperidine

Product 1

HCID 153920581-[5-(Dimethylaminosulfonylamino)indole-2-carbonyl]-4-[N-methyl-N-(3-(1-methylethylamino)-2-pyridinyl)amino]piperidine

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-[5-aminoindole-2-carbonyl]-4-[N-methyl-N-(3-(1-methylethylamino)-2-pyridinyl)amino]piperidine (PREPARATION 56, 91 mg) in pyridine (0.5 ml) under nitrogen is added N,N-dimethylsulfamoyl chloride. The mixture is stirred at 20°-25° for 16 hr and then diluted with methylene chloride (35 ml) and 1M hydrochloric acid (20 ml). The layers are separated and the organic layer is washed with 1M hydrochloric acid (20 ml) and saline, dried over sodium sulfate, and concentrated to give a solid film which is then chromatographed on two 2000 μ preparative silica gel plates, eluting with methanol/chloroform (5/95). The desired band is extracted and concentrated to give the title compound, NMR (CDCl3) 10.34, 7.72, 7.64, 7.56, 7.37, 7.16, 6.95, 6.84, 6.70, 4.65, 4.50, 3.56, 3.46, 3.40-3.00, 2.80, 2.63, 1.93, 1.64 and 1.22 δ.

Workup

  1. customThe layers are separated
  2. washthe organic layer is washed with 1M hydrochloric acid (20 ml) and saline
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customto give a solid film which
  6. customis then chromatographed on two 2000 μ preparative silica gel plates
  7. washeluting with methanol/chloroform (5/95)
  8. extractionThe desired band is extracted
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-a9902e96f74c4c8e9d366ac994a9d32c
Source dataset
uspto-grants-1997_11
Patent number
US05686610

Reaction notes

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