Dimethylformamide → HCID 69952117, compound

HRID 1699530Notes

Reaction equation

HRID 1699530 reaction equation
[C:1](=[O:4])([O-])[O-].[Cs+].[Cs+].[C:7]([C:9]1[N:10]([CH2:34][C:35]2[CH:40]=[CH:39][C:38]([O:41][CH3:42])=[CH:37][C:36]=2[O:43][CH3:44])[C:11](=[O:33])[N:12]([C:23]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[N:25]([CH3:32])[CH:24]=2)[C:13]=1[C:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[NH:16][CH:15]=1)#[N:8].[CH3:45][N:46]([CH:48]=[O:49])C>>[C:7]([C:9]1[N:10]([CH2:34][C:35]2[CH:40]=[CH:39][C:38]([O:41][CH3:42])=[CH:37][C:36]=2[O:43][CH3:44])[C:11](=[O:33])[N:12]([C:23]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[N:25]([CH3:32])[CH:24]=2)[C:13]=1[C:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:16]([C@H:9]2[CH2:13][CH2:14][C@H:45]([N:46]3[C:48](=[O:49])[C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[C:1]3=[O:4])[CH2:7]2)[CH:15]=1)#[N:8]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 183207294-Cyano-3-(2,4-dimethoxybenzyl)-5-(3-indolyl)-1-(1-methyl-3-indolyl)-2,3-dihydroimidazol-2-one

Product 1

HCID 69952117HCID 69952117, compoundYield 54%

Procedure

Two portions of totally 0.72 g (2.33 mmol) of 1(R)-O-Methanesulfonyl-3(S)-phthalimido-cyclopentane and two portions of totally 1.33 g (4.05 mmol) of cesium carbonate were added within 1.5 hours, to a stirred solution of 0.26 g (0.51 mmol) 4-cyano-3-(2,4-dimethoxybenzyl)-5-(3-indolyl)-1-(1-methyl-3-indolyl)-2,3-dihydroimidazol-2-one in 3 ml of dry DMF at 70° C. After an additional 2 hours, the reaction mixture was cooled to room temperature and partitioned between ethyl acetate and saturated brine. The aqeous phase was back-extracted with ethyl acetate and the combined organic extracts washed three times with saturated brine, dried over Na2SO4 and concentrated. The residue was purified by chromatography on SiO2 (EtOAc-heptane, 3:2). The fractions containing the desired product were combined and crystallized (chloroform:ether) to give the sub-title compound (0.20 g, 54%).

Workup

  1. custompartitioned between ethyl acetate and saturated brine
  2. extractionThe aqeous phase was back-extracted with ethyl acetate
  3. washthe combined organic extracts washed three times with saturated brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified by chromatography on SiO2 (EtOAc-heptane, 3:2)
  7. additionThe fractions containing the desired product
  8. customcrystallized (chloroform:ether)

Sources & evidence

ORD record
ord-fabd5a304e664462824c0548175737dd
Source dataset
uspto-grants-2002_02
Patent number
US06346625B1

Reaction notes

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