Dimethylformamide → HCID 59077488, compound

HRID 1359840Notes

Reaction equation

HRID 1359840 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 6228Dimethylformamide2×HCID 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 59077488HCID 59077488, compoundYield 30%

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 (200 mg, 0.4 mmol), HOBt (54 mg, 1 eq.) and EDAC (77 mg, 1 eq.) in DMF (1.5 mL) was stirred at rt for 10 mins. To the mixture was then added (R)-1-(S)-1-pyrrolidin-2-ylmethyl-pyrrolidin-3-ol (200 mg, 3 eq.) in DMF (1.5 mL). 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 79 mg (30%) 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-f6f96d992b77457e911f9d7da7aa4ea7
Source dataset
uspto-grants-2003_07
Patent number
US06599902B2

Reaction notes

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