1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 5-(2,6-Dichloro-phenylmethanesulfonyl)-3-[1-{3,5-dimethyl-4-[2-oxo-2-((s)-3-pyrrolidin-1-ylmethyl-piperidin-1-yl)-ethyl]-1h-pyrrol-2-yl}-meth-(z)-ylidene]-1,3-dihydro-indol-2-one

HRID 1359813Notes

Reaction equation

HRID 1359813 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[CH2:9][S:10]([C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[NH:18][C:17](=[O:22])/[C:16]/2=[CH:23]\[C:24]1[NH:28][C:27]([CH3:29])=[C:26]([CH2:30][C:31](O)=[O:32])[C:25]=1[CH3:34])(=[O:12])=[O:11].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.[N:56]1([CH2:61][C@@H:62]2[CH2:67][CH2:66][CH2:65][NH:64][CH2:63]2)[CH2:60][CH2:59][CH2:58][CH2:57]1>CN(C=O)C>[Cl:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=1[CH2:9][S:10]([C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[NH:18][C:17](=[O:22])/[C:16]/2=[CH:23]\[C:24]1[NH:28][C:27]([CH3:29])=[C:26]([CH2:30][C:31](=[O:32])[N:64]2[CH2:65][CH2:66][CH2:67][C@@H:62]([CH2:61][N:56]3[CH2:57][CH2:58][CH2:59][CH2:60]3)[CH2:63]2)[C:25]=1[CH3:34])(=[O:12])=[O:11]

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 7183063(r)-3-Pyrrolidin-1-ylmethyl-piperidineHCID 59077497HCID 59077497, compound

Product 1

HCID 590775165-(2,6-Dichloro-phenylmethanesulfonyl)-3-[1-{3,5-dimethyl-4-[2-oxo-2-((s)-3-pyrrolidin-1-ylmethyl-piperidin-1-yl)-ethyl]-1h-pyrrol-2-yl}-meth-(z)-ylidene]-1,3-dihydro-indol-2-oneYield 85.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of {5-[5-(2,6-dichloro-phenylmethanesulfonyl)-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-2,4-dimethyl-1H-pyrrol-3-yl}-acetic acid (156 mg, 0.3 mmol), HOBt (80 mg) and EDAC (110 mg) in DMF (4 mL) was added TEA (3 drops). After stirring at rt for 2 hours, to the mixture was added (R)-3-pyrrolidin-1-ylmethyl-piperidine (250 mg). After stirring at rt for overnight, the reaction was concentrated and dissolved in ethyl acetate. It was then washed with water and sodium bicarbonate, dried and concentrated. The residue was purified on a silica gel column to give 172 mg of the titled compound. MS m/z 667 [M−1].

Workup

  1. stirringAfter stirring at rt for overnight
  2. concentrationthe reaction was concentrated
  3. dissolutiondissolved in ethyl acetate
  4. washIt was then washed with water and sodium bicarbonate
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was purified on a silica gel column

Sources & evidence

ORD record
ord-c8e3791ac7904ebf8f75effd224959a1
Source dataset
uspto-grants-2003_07
Patent number
US06599902B2

Reaction notes

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