1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → (S)-N-(1-(benzyl(2,2-diethoxyethyl)amino)-1-oxopropan-2-yl)-3-(3-benzylureido)thiophene-2-carboxamide

HRID 576886Notes

Reaction equation

HRID 576886 reaction equation
[CH2:1]([NH:8][C:9](=[O:19])[NH:10][C:11]1[CH:15]=[CH:14][S:13][C:12]=1[C:16]([OH:18])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ON1C2C=CC=CC=2N=N1.C(N=C=NCCCN(C)C)C.[NH2:41][C@@H:42]([CH3:61])[C:43]([N:45]([CH2:54][C:55]1[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=1)[CH2:46][CH:47]([O:51][CH2:52][CH3:53])[O:48][CH2:49][CH3:50])=[O:44]>ClCCl>[CH2:54]([N:45]([CH2:46][CH:47]([O:48][CH2:49][CH3:50])[O:51][CH2:52][CH3:53])[C:43](=[O:44])[C@@H:42]([NH:41][C:16]([C:12]1[S:13][CH:14]=[CH:15][C:11]=1[NH:10][C:9]([NH:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:19])=[O:18])[CH3:61])[C:55]1[CH:56]=[CH:57][CH:58]=[CH:59][CH:60]=1

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 533974903-(3-Benzylureido)thiophene-2-carboxylic acidHCID 66644890(S)-2-amino-N-benzyl-N-(2,2-diethoxyethyl)propanamide

Product 1

HCID 49806036(S)-N-(1-(benzyl(2,2-diethoxyethyl)amino)-1-oxopropan-2-yl)-3-(3-benzylureido)thiophene-2-carboxamideYield 54%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 3-(3-benzylureido)thiophene-2-carboxylic acid (Compound V-1) 49.7 mg (0.18 mmol) and N-hydroxybenzotriazol 6.1 mg (0.045 mmol) in dichloromethane 1 ml, 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide 43.1 mg (0.225 mmol) was added and the mixture was stirred at room temperature for 0.5 hr. A solution of (S)-2-amino-N-benzyl-N-(2,2-diethoxyethyl)propanamide (Compound VI-1) 44.2 mg (0.15 mmol) in dichloromethane 1 ml was added to the reaction mixture and the mixture was stirred at room temperature for 18 hrs. The reaction mixture was washed with sat. NaHCO3 aq. 1 ml, water 1 ml and brine 1 ml. The organic phase was filtered on celite 1 g and magnesium sulfate 150 mg. The mother solution was concentrated in vacuo and the residue was purified with PTLC (development solvent: chloroform:methanol=98:2) to obtain the titled compound 44.7 mg (54%).

Workup

  1. stirringthe mixture was stirred at room temperature for 18 hrs
  2. washThe reaction mixture was washed with sat. NaHCO3 aq. 1 ml, water 1 ml and brine 1 ml
  3. filtrationThe organic phase was filtered on celite 1 g and magnesium sulfate 150 mg
  4. concentrationThe mother solution was concentrated in vacuo
  5. customthe residue was purified with PTLC (development solvent: chloroform:methanol=98:2)

Sources & evidence

ORD record
ord-bcf29079242e4f149a3dfcdf6eebc28f
Source dataset
uspto-grants-2015_05
Patent number
US09040531B2

Reaction notes

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