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

HRID 1359870Notes

Reaction equation

HRID 1359870 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][CH2:31][C:32](O)=[O:33])[C:25]=1[CH3:35])(=[O:12])=[O:11].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[N:57]1([CH2:62][C@H:63]2[CH2:67][CH2:66][CH2:65][NH:64]2)[CH2:61][CH2:60][CH2:59][CH2:58]1>CN(C=O)C.O.C([O-])(O)=O.[Na+]>[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][CH2:31][C:32](=[O:33])[N:64]2[CH2:65][CH2:66][CH2:67][C@@H:63]2[CH2:62][N:57]2[CH2:61][CH2:60][CH2:59][CH2:58]2)[C:25]=1[CH3:35])(=[O:11])=[O:12]

Participants

8

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 853151(R)-(-)-1-(2-Pyrrolidinylmethyl)pyrrolidineHCID 590776223-{5-[5-(2,6-Dichloro-phenylmethanesulfonyl)-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-2,4-dimethyl-1H-pyrrol-3-yl}-propionic Acid

Product 1

HCID 590777235-(2,6-Dichloro-phenylmethanesulfonyl)-3-[1-{3,5-dimethyl-4-[3-oxo-3-((r)-2-pyrrolidin-1-ylmethyl-pyrrolidin-1-yl)-propyl]-1h-pyrrol-2-yl}-meth-(z)-ylidene]-1,3-dihydro-indol-2-one

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a mixture of 3-{5-[5-(2,6-dichloro-phenylmethanesulfonyl)-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-2,4-dimethyl-1H-pyrrol-3-yl}-propionic acid (178 mg, 0.33 mmol), EDAC (97 mg, 0.51 mmol) and HOBt (67 mg, 0.5 mmol) in DMF (4 mL) was added (R)-2-pyrrolidin-1-ylmethyl-pyrrolidine (106 mg, 0.68 mmol) and TEA (0.1 mL). The mixture was stirred at rt for 20 hours. The reaction was diluted with water and NaHCO3, extracted with DCM. The combined DCM was concentrated and the residue was purified on a silica gel column to give the titled compound.

Workup

  1. extractionextracted with DCM
  2. concentrationThe combined DCM was concentrated
  3. customthe residue was purified on a silica gel column

Sources & evidence

ORD record
ord-b819eb78c8c648e9befbd25bf24ff633
Source dataset
uspto-grants-2003_07
Patent number
US06599902B2

Reaction notes

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