1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 59077542, compound

HRID 1359815Notes

Reaction equation

HRID 1359815 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].[F:34][C:35]([F:41])([F:40])[CH2:36][NH:37][CH2:38]N.C1C=CC2N(O)N=[N:48][C:46]=2C=1.CCN=C=NCCCN(C)C>CN(C=O)C>[F:34][C:35]([F:41])([F:40])[CH2:36][NH:37][CH2:38][CH2:46][NH:48][C:30]([C:26]1[C:25]([CH3:33])=[C:24](/[CH:23]=[C:16]2\[C:17](=[O:22])[NH:18][C:19]3[C:15]\2=[CH:14][C:13]([S:10]([CH2:9][C:3]2[C:2]([Cl:1])=[CH:7][CH:6]=[CH:5][C:4]=2[Cl:8])(=[O:11])=[O:12])=[CH:21][CH:20]=3)[NH:28][C:27]=1[CH3:29])=[O:32]

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 18179828HCID 18179828, 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 59077542HCID 59077542, compoundYield 69%

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 (95 mg, 0.19 mmol), N-(2,2,2-trifluoro-ethyl)-methanediamine (59 mg, 0.41 mmol), HOBt (41 mg, 0.3 mmol), EDAC (59 mg, 0.31 mmol) and TEA (0.06 mL) in DMF (3 mL) was stirred at rt for 48 hours. The reaction was concentrated, diluted with sodium bicarbonate and extracted with DCM (2×). The combined DCM was washed with brine, dried and concentrated. The residue was purified on a silica gel column to give 82 mg (69%) of the titled compound.

Workup

  1. concentrationThe reaction was concentrated
  2. additiondiluted with sodium bicarbonate
  3. extractionextracted with DCM (2×)
  4. washThe combined DCM was washed with brine
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was purified on a silica gel column

Sources & evidence

ORD record
ord-9129ea57ec6c468b8c30e89bce5d774b
Source dataset
uspto-grants-2003_07
Patent number
US06599902B2

Reaction notes

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