1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 59077682, compound

HRID 1359844Notes

Reaction equation

HRID 1359844 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].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.[CH:55]1([NH:58][C:59]([C@@H:61]2[CH2:66][CH2:65][CH2:64][NH:63][CH2:62]2)=[O:60])[CH2:57][CH2:56]1>CN(C=O)C.C(Cl)Cl>[CH:55]1([NH:58][C:59]([C@@H:61]2[CH2:66][CH2:65][CH2:64][N:63]([C:30]([C:26]3[C:25]([CH3:33])=[C:24](/[CH:23]=[C:16]4\[C:17](=[O:22])[NH:18][C:19]5[C:15]\4=[CH:14][C:13]([S:10]([CH2:9][C:3]4[C:2]([Cl:1])=[CH:7][CH:6]=[CH:5][C:4]=4[Cl:8])(=[O:11])=[O:12])=[CH:21][CH:20]=5)[NH:28][C:27]=3[CH3:29])=[O:32])[CH2:62]2)=[O:60])[CH2:57][CH2:56]1

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 28163028HCID 28163028, compoundHCID 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 59077682HCID 59077682, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

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 (250 mg, 0.5 mmol), HOBt (65 mg), EDAC (191 mg), (R)-piperidine-3-carboxylic acid cyclopropylamide (250 mg) and TEA (7 drops) in DMF (3 mL) was stirred at rt for overnight. The reaction was diluted with DCM, washed with water, 10% sodium carbonate, dried and concentrated. The residue was purified on a silica gel column to give 200 mg of the titled compound.

Workup

  1. washwashed with water, 10% sodium carbonate
  2. customdried
  3. concentrationconcentrated
  4. customThe residue was purified on a silica gel column

Sources & evidence

ORD record
ord-ac49a6d1c9e74efe9f6fdcf2572c0c46
Source dataset
uspto-grants-2003_07
Patent number
US06599902B2

Reaction notes

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