1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 59077633, compound

HRID 1359814Notes

Reaction equation

HRID 1359814 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]([CH2:30][C:31]([OH:33])=O)[C:25]=1[CH3:34])(=[O:12])=[O:11].[F:35][C:36]([F:43])([F:42])[CH2:37][NH:38][CH2:39][CH2:40][NH2:41].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C>CN(C=O)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]([CH2:30][C:31]([NH:41][CH2:40][CH2:39][NH:38][CH2:37][C:36]([F:43])([F:42])[F:35])=[O:33])[C:25]=1[CH3:34])(=[O:11])=[O:12]

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 18179872HCID 18179872, compoundHCID 59077497HCID 59077497, compound

Product 1

HCID 59077633HCID 59077633, compoundYield 72.2%

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-pyrrol-3-yl}-acetic acid (267 mg, 0.51 mmol), N-(2,2,2-trifluoro-ethyl)-ethane-1,2-diamine (123 mg, 0.86 mmol), HOBt (104 mg, 0.77 mmol), EDAC (154 mg, 0.81 mmol) and TEA (0.14 mL, 1 mmol) in DMF (3 mL) was stirred At rt for 48 hours. The reaction was concentrated, diluted with sat. sodium bicarbonate and extracted with DCM. The organic layer was washed with brine, dried and purified on a silica gel column to give 237 mg (72%) of the titled compound.

Workup

  1. concentrationThe reaction was concentrated
  2. additiondiluted with sat. sodium bicarbonate
  3. extractionextracted with DCM
  4. washThe organic layer was washed with brine
  5. customdried
  6. custompurified on a silica gel column

Sources & evidence

ORD record
ord-c625b226c12440339f3248eefea43a86
Source dataset
uspto-grants-2003_07
Patent number
US06599902B2

Reaction notes

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