1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 59077536, compound

HRID 1359837Notes

Reaction equation

HRID 1359837 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([N:37]([CH3:44])[CH2:38][C@@H:39]2[CH2:43][CH2:42][CH2:41][NH:40]2)[CH2:36][CH2:35]1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C>CN(C=O)C>[CH:34]1([N:37]([CH2:38][C@@H:39]2[CH2:43][CH2:42][CH2:41][N:40]2[C:30]([C:26]2[C:25]([CH3:33])=[C:24](/[CH:23]=[C:16]3\[C:17](=[O:22])[NH:18][C:19]4[C:15]\3=[CH:14][C:13]([S:10]([CH2:9][C:3]3[C:4]([Cl:8])=[CH:5][CH:6]=[CH:7][C:2]=3[Cl:1])(=[O:11])=[O:12])=[CH:21][CH:20]=4)[NH:28][C:27]=2[CH3:29])=[O:32])[CH3:44])[CH2:35][CH2:36]1

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 45088411N-Methyl-N-{[(2S)-pyrrolidin-2-yl]methyl}cyclopropanamineHCID 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 59077536HCID 59077536, compound

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-pyrrole-3-carboxylic acid (165 mg, 0.33 mmol), cyclopropyl-methyl-(S)-1-pyrrolidin-2-ylmethyl-amine (65 mg, 0.46 mmol), HOBt (687 mg, 0.5 mmol), EDAC (101 mg, 0.53 mmol) and TEA (0.1 mL) in DMF (4 mL) was stirred at rt for 48 hours. The reaction was concentrated, diluted with sodium bicarbonate, extracted with DCM. The combined DCM was dried, concentrated and purified on a silica gel column to give the titled compound.

Workup

  1. concentrationThe reaction was concentrated
  2. additiondiluted with sodium bicarbonate
  3. extractionextracted with DCM
  4. dry with materialThe combined DCM was dried
  5. concentrationconcentrated
  6. custompurified on a silica gel column

Sources & evidence

ORD record
ord-eb84cf63bd9f4a9b99b5c4f3ecd50867
Source dataset
uspto-grants-2003_07
Patent number
US06599902B2

Reaction notes

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