1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 75290664, compound

HRID 1443514Notes

Reaction equation

HRID 1443514 reaction equation
[CH3:1][O:2][C:3]1[C:12]([CH3:13])=[C:11]2[C:6]([C:7]([O:20][CH:21]3[CH2:38][CH:37]4[N:23]([C:24](=[O:44])[N:25]([CH3:43])[CH2:26][CH2:27][CH2:28][CH2:29][CH:30]=[CH:31][CH:32]5[C:34]([C:40]([OH:42])=O)([NH:35][C:36]4=[O:39])[CH2:33]5)[CH2:22]3)=[N:8][C:9]([C:14]3[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=3)=[N:10]2)=[CH:5][CH:4]=1.CCN=C=NCCCN(C)C.[CH:56]1([S:59]([NH2:62])(=[O:61])=[O:60])[CH2:58][CH2:57]1.C1CCN2C(=NCCC2)CC1>ClCCl>[CH3:1][O:2][C:3]1[C:12]([CH3:13])=[C:11]2[C:6]([C:7]([O:20][CH:21]3[CH2:38][CH:37]4[N:23]([C:24](=[O:44])[N:25]([CH3:43])[CH2:26][CH2:27][CH2:28][CH2:29][CH:30]=[CH:31][CH:32]5[C:34]([C:40]([NH:62][S:59]([CH:56]6[CH2:58][CH2:57]6)(=[O:61])=[O:60])=[O:42])([NH:35][C:36]4=[O:39])[CH2:33]5)[CH2:22]3)=[N:8][C:9]([C:14]3[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=3)=[N:10]2)=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 15765418CyclopropanesulfonamideHCID 68411028HCID 68411028, compound

Product 1

HCID 75290664HCID 75290664, compoundYield 73.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

The acid 178 (67 mg, 0.11 mmol) and EDAC (26 mg, 0.13 mmol) were dissolved in dichloromethane (3 ml). After stirring at room temperature for 5 h the mixture was diluted with dichloromethane (10 ml) and the organic phase were washed with water and dried (sodium sulphate). The volume was then reduced to 2 ml and cyclopropyl sulphonamide (20 mg, 0.17 mmol) and DBU (36 mg, 2.3 mmol) were added. The mixture was allowed to stir over-night at room temperature and then washed using 5% aqueous citric acid. Purification by chromatography (0 to 2% methanol in dichloromethane gave the title compound (57 mg, 73%), MS (M+H)+ 704.

Workup

  1. washthe organic phase were washed with water
  2. dry with materialdried (sodium sulphate)
  3. additionwere added
  4. stirringto stir over-night at room temperature
  5. washwashed
  6. customPurification by chromatography (0 to 2% methanol in dichloromethane

Sources & evidence

ORD record
ord-8f7ff46682604949bc81c4337d0b0d92
Source dataset
uspto-grants-2010_02
Patent number
US07659245B2

Reaction notes

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