1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 178432702, compound

HRID 1670660Notes

Reaction equation

HRID 1670660 reaction equation
[C:1]([C:4]1[N:9]=[C:8]([C:10]2[CH:15]=[CH:14][C:13]([C@H:16]3[CH2:21][CH2:20][C@H:19]([CH2:22][C:23](O)=[O:24])[CH2:18][CH2:17]3)=[CH:12][CH:11]=2)[C:7]([CH3:26])=[N:6][C:5]=1[CH3:27])(=[O:3])[NH2:2].CCN=C=NCCCN(C)C.[CH3:39][S:40]([NH2:43])(=[O:42])=[O:41]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH3:27][C:5]1[C:4]([C:1]([NH2:2])=[O:3])=[N:9][C:8]([C:10]2[CH:11]=[CH:12][C:13]([C@H:16]3[CH2:17][CH2:18][C@H:19]([CH2:22][C:23]([NH:43][S:40]([CH3:39])(=[O:42])=[O:41])=[O:24])[CH2:20][CH2:21]3)=[CH:14][CH:15]=2)=[C:7]([CH3:26])[N:6]=1

Participants

6

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 72879MethanesulfonamideHCID 178432703HCID 178432703, compound

Product 1

HCID 178432702HCID 178432702, compoundYield 60.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of Example 1 (30 mg, 0.082 mmol) in DCM was added DMAP (2 mg, 0.02 mmol), TEA (16 μL, 0.122 mmol), EDCI (20 mg, 0.11 mmol) and finally methanesulfonamide (11 mg, 0.11 mmol, CAS 3144-09-0). The solution was stirred at RT overnight. The crude was concentrated and purified by HPLC (acidic). Evaporation and co-evaporation with toluene gave title compound (22 mg, 60%).

Workup

  1. concentrationThe crude was concentrated
  2. custompurified by HPLC (acidic)
  3. customEvaporation and co-evaporation with toluene

Sources & evidence

ORD record
ord-13f674c7a042406cb83c18115c6ee589
Source dataset
uspto-grants-2011_08
Patent number
US07994179B2

Reaction notes

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