Pyridine → 1-[5-(Methanesulfonamido)indole-2-carbonyl]-4-[3-(1,1-dimethylpropylamino)-2-pyridinyl]piperazine

HRID 2293783Notes

Reaction equation

HRID 2293783 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][N:16]([C:19]3[C:24]([NH:25][C:26]([CH3:30])([CH3:29])[CH2:27][CH3:28])=[CH:23][CH:22]=[CH:21][N:20]=3)[CH2:15][CH2:14]1)=[O:12])=[CH:5]2.N1C=CC=CC=1.[CH3:37][S:38](Cl)(=[O:40])=[O:39]>C(Cl)Cl.O>[CH3:37][S:38]([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][N:16]([C:19]3[C:24]([NH:25][C:26]([CH3:29])([CH3:30])[CH2:27][CH3:28])=[CH:23][CH:22]=[CH:21][N:20]=3)[CH2:15][CH2:14]1)=[O:12])=[CH:5]2)(=[O:40])=[O:39]

Participants

6

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 214776001-[5-Aminoindole-2-carbonyl]-4-[3-(1,1-dimethylpropylamino)-2-pyridinyl]piperazine

Product 1

HCID 214776751-[5-(Methanesulfonamido)indole-2-carbonyl]-4-[3-(1,1-dimethylpropylamino)-2-pyridinyl]piperazine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1-[5-aminoindole-2-carbonyl]-4-[3-(1,1-dimethylpropylamino)-2-pyridinyl]piperazine (EXAMPLE 41, 300 mg) in dry methylene chloride (6 ml) under nitrogen is added pyridine (119 μl) and methanesulfonyl chloride (57 μl). The mixture is stirred at 20°-25° for 24 hr and then diluted with methylene chloride (20 ml) and water (8 ml). The layers are separated and the organic phase is washed with saline (8 ml), dried over sodium sulfate, and concentrated to give a solid which is then chromatographed on silica gel (230-400 mesh, 34 g, 5-6 psi), eluting with methanol/chloroform (2.5/97.5). Pooling of the appropriate fractions, concentration to a solid, and recrystallization from chloroform gives the title compound, mp 232°-233° (decomp).

Workup

  1. customThe layers are separated
  2. washthe organic phase is washed with saline (8 ml)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customto give a solid which
  6. customis then chromatographed on silica gel (230-400 mesh, 34 g, 5-6 psi)
  7. washeluting with methanol/chloroform (2.5/97.5)
  8. concentrationPooling of the appropriate fractions, concentration
  9. customto a solid, and recrystallization from chloroform

Sources & evidence

ORD record
ord-efb7e84fb2dd43fda299725da674fa9b
Source dataset
uspto-grants-1997_11
Patent number
US05686610

Reaction notes

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