Dimethylformamide → HCID 59077707, compound

HRID 1359841Notes

Reaction equation

HRID 1359841 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]([C:30]([OH:32])=O)[C:25]=1[CH3:33])(=[O:12])=[O:11].[CH:34]1[CH:35]=CC2N(O)N=[N:40][C:38]=2[CH:39]=1.CCN=C=N[CH2:49][CH2:50][CH2:51][N:52]([CH3:54])[CH3:53].CN(C=[O:59])C>>[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]([C:30]([N:40]2[CH2:35][CH2:34][CH2:39][C@@H:38]2[CH2:54][N:52]2[CH2:51][CH2:50][C@@H:49]([OH:59])[CH2:53]2)=[O:32])[C:25]=1[CH3:33])(=[O:11])=[O:12]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 590775075-[5-(2,6-dichloro-phenylmethanesulfonyl)-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-2,4-dimethyl-1H-pyrrole-3-carboxylic acid

Product 1

HCID 59077707HCID 59077707, compoundYield 61%

Procedure

A mixture of 5-[5-(2,6-dichloro-phenylmethanesulfonyl)-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-2,4-dimethyl-1H-pyrrole-3-carboxylic acid (0.2 g, 0.4 mmol), HOBt (54 mg, 1 eq.), EDAC (77 mg, 1 eq.) in DMF (1.5 mL) was stirred at rt for 10 mins. To the mixture was added (R)-1-(R)-1-pyrrolidin-2-ylmethyl-pyrrolidin-3-ol (0.2 g, 3 eq.). After stirring at rt for over the weekend, the precipitate was collected by vacuum filtration, washed with water, sodium bicarbonate and water, and then dried. The solid was purified on a silica gel column to give 159 mg (61%) of the titled compound.

Workup

  1. stirringAfter stirring at rt for over the weekend
  2. filtrationthe precipitate was collected by vacuum filtration
  3. washwashed with water, sodium bicarbonate and water
  4. customdried
  5. customThe solid was purified on a silica gel column

Sources & evidence

ORD record
ord-29cce4267d3e4fbbbd089146844c4521
Source dataset
uspto-grants-2003_07
Patent number
US06599902B2

Reaction notes

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