1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 68489988, compound

HRID 21011Notes

Reaction equation

HRID 21011 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([C:17](O)=[O:18])=[CH:14][CH:15]=2)[CH:10]=[C:9]1[C:20]1[CH:21]=[CH:22][C:23]([Cl:30])=[C:24]2[C:28]=1[C:27](=[O:29])[NH:26][CH2:25]2)=[O:7])([CH3:4])([CH3:3])[CH3:2].CCN=C=NCCCN(C)C.C1C=C2N=NN(O)C2=CC=1.O.[C:53]([O:57][C:58]([N:60]1[CH2:65][CH2:64][NH:63][CH2:62][CH2:61]1)=[O:59])([CH3:56])([CH3:55])[CH3:54]>CN(C=O)C.O>[Cl:30][C:23]1[CH:22]=[CH:21][C:20]([C:9]2[N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[C:16]3[C:11]([CH:10]=2)=[CH:12][C:13]([C:17]([N:63]2[CH2:62][CH2:61][N:60]([C:58]([O:57][C:53]([CH3:56])([CH3:55])[CH3:54])=[O:59])[CH2:65][CH2:64]2)=[O:18])=[CH:14][CH:15]=3)=[C:28]2[C:24]=1[CH2:25][NH:26][C:27]2=[O:29]

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 143452tert-Butyl piperazine-1-carboxylateHCID 27960291-Hydroxybenzotriazole hydrateHCID 68490974HCID 68490974, compound

Product 1

HCID 68489988HCID 68489988, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

In a similar manner to Example 20, 7-[1-(tert-butoxycarbonyl)-5-carboxyindol-2-yl]-4-chloroisoindolinone (37.8 mg, 0.0886 mmol) was dissolved in DMF (1 mL), and the solution was treated with EDCI (34 mg, 0.18 mmol), HOBT monohydrate (12 mg, 0.089 mmol) and 1-(tert-butoxycarbonyl)piperazine (66 mg, 0.35 mmol). The mixture was added with water and the precipitated solid was collected by filtration, washed with water and then dried under reduced pressure to obtain 4-chloro-7-(1-(tert-butoxycarbonyl)-5-[-4-(tert-butoxycarbonyl)piperazin-1-ylcarbonyl]indol-2-yl)isoindolinone (43.5 mg, yield 83%).

Workup

  1. filtrationthe precipitated solid was collected by filtration
  2. washwashed with water
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-bb2fd94eb32846b48452ffcf433e7ec6
Source dataset
uspto-grants-2010_06
Patent number
US07745641B2

Reaction notes

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