1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 10211554, compound

HRID 1359832Notes

Reaction equation

HRID 1359832 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].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.[CH:56]1([CH2:59][N:60]2[CH2:65][CH2:64][NH:63][CH2:62][CH2:61]2)[CH2:58][CH2:57]1>CN(C=O)C>[CH:56]1([CH2:59][N:60]2[CH2:65][CH2:64][N:63]([C:31](=[O:33])[CH2:30][C:26]3[C:25]([CH3:34])=[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:12])=[O:11])=[CH:21][CH:20]=5)[NH:28][C:27]=3[CH3:29])[CH2:62][CH2:61]2)[CH2:58][CH2:57]1

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 9658751-(Cyclopropylmethyl)piperazineHCID 59077497HCID 59077497, compound

Product 1

HCID 10211554HCID 10211554, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

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 (210 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 30 mins. To the mixture was added 1-cyclopropylmethyl-piperazine (112 mg, 2 eq.) in DMF (1.5 mL). After stirring at rt for overnight, the precipitate was collected by vacuum filtration, washed with water, sodium bicarbonate and water and then dried to give 240 mg (94%) of the titled compound.

Workup

  1. stirringAfter stirring at rt for overnight
  2. filtrationthe precipitate was collected by vacuum filtration
  3. washwashed with water, sodium bicarbonate and water
  4. customdried

Sources & evidence

ORD record
ord-67c70bad2f204a6c971a4f584f307458
Source dataset
uspto-grants-2003_07
Patent number
US06599902B2

Reaction notes

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