1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 75277260, compound

HRID 1429176Notes

Reaction equation

HRID 1429176 reaction equation
[C:1]1([C:7]2[N:12]=[C:11]([O:13][CH:14]3[CH2:31][CH:30]4[CH:16]([C:17](=[O:37])[N:18]([CH3:36])[CH2:19][CH2:20][CH2:21][CH2:22][CH:23]=[CH:24][CH:25]5[C:27]([C:33](O)=[O:34])([NH:28][C:29]4=[O:32])[CH2:26]5)[CH2:15]3)[CH:10]=[C:9]([C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:44]1([S:47]([NH2:50])(=[O:49])=[O:48])[CH2:46][CH2:45]1.CCN=C=NCCCN(C)C.C1CCN2C(=NCCC2)CC1>C(Cl)Cl>[C:1]1([C:7]2[N:12]=[C:11]([O:13][CH:14]3[CH2:31][CH:30]4[CH:16]([C:17](=[O:37])[N:18]([CH3:36])[CH2:19][CH2:20][CH2:21][CH2:22][CH:23]=[CH:24][CH:25]5[C:27]([C:33]([NH:50][S:47]([CH:44]6[CH2:46][CH2:45]6)(=[O:49])=[O:48])=[O:34])([NH:28][C:29]4=[O:32])[CH2:26]5)[CH2:15]3)[CH:10]=[C:9]([C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 15765418CyclopropanesulfonamideHCID 68589773HCID 68589773, compound

Product 1

HCID 75277260HCID 75277260, compoundYield 62.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The acid 17f (240 mg, 0.41 mmol) was reacted with cyclopropane sulfonamide (63 mg, 0.52 mmol), EDAC (105 mg, 0.55 mmol) and DBU (182 mg, 1.2 mmol) in dry DCM according to the procedure described in Example 13 step f. Purification by column chromatography on silica gel eluted with diethyl ether-ethyl acetate gave the title compound, (175 mg, 62%), (M+H)+684.

Workup

  1. customPurification by column chromatography on silica gel
  2. washeluted with diethyl ether-ethyl acetate

Sources & evidence

ORD record
ord-370b4b02906843a48613ae9e118daecf
Source dataset
uspto-grants-2015_01
Patent number
US08937080B2

Reaction notes

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