Dimethylformamide → HCID 59077505, compound

HRID 1359812Notes

Reaction equation

HRID 1359812 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]([OH:33])=O)[C:25]=1[CH3:34])(=[O:12])=[O:11].[CH:35]1[CH:36]=CC2N(O)N=[N:41][C:39]=2[CH:40]=1.CCN=C=N[CH2:50][CH2:51][CH2:52][N:53]([CH3:55])[CH3:54].CN(C=[O:60])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]([N:41]2[CH2:36][CH2:35][CH2:40][C@H:39]2[CH2:55][N:53]2[CH2:52][CH2:51][C@@H:50]([OH:60])[CH2:54]2)=[O:33])[C:25]=1[CH3:34])(=[O:12])=[O:11]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 59077497HCID 59077497, compound

Product 1

HCID 59077505HCID 59077505, compound

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)-1-(S)-1-pyrrolidin-2-ylmethyl-pyrrolidin-3-ol (300 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 210 mg of the titled compound. MS m/z 671 [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-b60ebe03f2714d588c34c79f2609a1f4
Source dataset
uspto-grants-2003_07
Patent number
US06599902B2

Reaction notes

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