Pyridine → 1-[5-(2-Phthalimidoethanesulfonamido)indole-2-carbonyl]-4-[N-methyl-N-(3-(1-methylethylamino)-2-pyridinyl)amino]piperidine

HRID 2293779Notes

Reaction equation

HRID 2293779 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.N1C=CC=CC=1.[C:37]1(=[O:53])[N:41]([CH2:42][CH2:43][S:44](Cl)(=[O:46])=[O:45])[C:40](=[O:48])[C:39]2=[CH:49][CH:50]=[CH:51][CH:52]=[C:38]12>C(Cl)Cl.O>[C:40]1(=[O:48])[N:41]([CH2:42][CH2:43][S:44]([NH:1][C:2]2[CH:3]=[C:4]3[C:8](=[CH:9][CH:10]=2)[NH:7][C:6]([C:11]([N:13]2[CH2:18][CH2:17][CH:16]([N:19]([CH3:30])[C:20]4[C:25]([NH:26][CH:27]([CH3:28])[CH3:29])=[CH:24][CH:23]=[CH:22][N:21]=4)[CH2:15][CH2:14]2)=[O:12])=[CH:5]3)(=[O:45])=[O:46])[C:37](=[O:53])[C:38]2=[CH:52][CH:51]=[CH:50][CH:49]=[C:39]12

Participants

6

Reactant 3

HCID 1049PyridineHCID 3087392-Phthalimidoethanesulfonyl chlorideHCID 153920561-[5-aminoindole-2-carbonyl]-4-[N-methyl-N-(3-(1-methylethylamino)-2-pyridinyl)amino]piperidine

Product 1

HCID 214776561-[5-(2-Phthalimidoethanesulfonamido)indole-2-carbonyl]-4-[N-methyl-N-(3-(1-methylethylamino)-2-pyridinyl)amino]piperidine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1-[5-aminoindole-2-carbonyl]-4-[N-methyl-N-(3-(1-methylethylamino)-2-pyridinyl)amino]piperidine (PREPARATION 56, 606 mg) in dry methylene chloride (5 ml) under nitrogen is added pyridine (127 μl, 1.05 equivalents) and 2-phthalimidoethanesulfonyl chloride (400 mg). The mixture is stirred at 20°-25° for 3 days and then diluted with methylene chloride (40 ml) and water (20 ml). The layers are separated and the organic phase is washed with saline (15 ml), dried over sodium sulfate, and concentrated under reduced pressure to give a residue which is then chromatographed on silica gel (230-400 mesh, 85 g, 8 psi), eluting with a gradient of methanol/chloroform (1/99-2.5/97.5). The appropriate fractions (Rf =0.33, TLC, methanol/chloroform, 5/95) are pooled and concentrated to give the title compound, NMR (CDCl3) 10.33, 7.80, 7.76-7.63, 7.35, 7.22, 6.95, 6.85, 6.69, 4.65, 4.51, 4.13, 3.60-3.40, 3.40-2.90, 2.64, 1.94, 1.65 and 1.22 δ.

Workup

  1. customThe layers are separated
  2. washthe organic phase is washed with saline (15 ml)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customto give a residue which
  6. customis then chromatographed on silica gel (230-400 mesh, 85 g, 8 psi)
  7. washeluting with a gradient of methanol/chloroform (1/99-2.5/97.5)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-17f078d823234ee082a6355f0dceb09a
Source dataset
uspto-grants-1997_11
Patent number
US05686610

Reaction notes

Loading…