Pyrrolidine → HCID 10675838, compound

HRID 2414296Notes

Reaction equation

HRID 2414296 reaction equation
Br[C:2]1[C:3](=[O:41])[N:4]([CH3:40])[C:5](=[O:39])[C:6]=1[C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[NH:9][C:8]=1[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]1[NH:22][C:23]2[C:28]([C:29]=1[C:30]1[C:31](=[O:38])[N:32]([CH3:37])[C:33](=[O:36])[C:34]=1Br)=[CH:27][CH:26]=[CH:25][CH:24]=2.[NH:42]1[CH2:46][CH2:45][CH2:44][CH2:43]1>>[CH3:40][N:4]1[C:5](=[O:39])[C:6]([C:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[NH:9][C:8]=2[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]2[NH:22][C:23]3[C:28]([C:29]=2[C:30]2[C:31](=[O:38])[N:32]([CH3:37])[C:33](=[O:36])[C:34]=2[N:42]2[CH2:46][CH2:45][CH2:44][CH2:43]2)=[CH:27][CH:26]=[CH:25][CH:24]=3)=[C:2]([N:4]2[CH2:5][CH2:6][CH2:2][CH2:3]2)[C:3]1=[O:41]

Participants

3

Reactant 2

HCID 31268PyrrolidineHCID 11802662HCID 11802662, compound

Product 1

HCID 10675838HCID 10675838, compound

Procedure

1.0 g (1.5 mmol) of 3-bromo-4-(2-(5-(3-(4-bromo-1-methyl-2,5-dioxo-2,5-dihydro-1H-3-pyrrolyl)-1H-2-indolyl)pentyl)-1H-3-indolyl)-1-methyl-2,5-dihydro-1H-pyrrole-2,5-dione is dissolved in 5 ml (60.6 mmol) of pyrrolidine and stirred overnight at room temp. Excess pyrrolidine is then distilled off. The residue is completely freed from solvent residues in an oil-pump vacuum and then purified by column chromatography (SiO2, CH2Cl2/ethyl acetate 95:5). Yield: 480 mg (49%).

Workup

  1. distillationExcess pyrrolidine is then distilled off
  2. custompurified by column chromatography (SiO2, CH2Cl2/ethyl acetate 95:5)

Sources & evidence

ORD record
ord-3b877ada47454311892da06762468501
Source dataset
uspto-grants-2004_11
Patent number
US06812243B2

Reaction notes

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