1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → Methyl 2-[4-({[2-[(tert-butoxycarbonyl)amino]-5-(3-thienyl)phenyl]amino}carbonyl)phenyl]-3-{[(methylamino)carbonyl]-amino}propanoate

HRID 1919910Notes

Reaction equation

HRID 1919910 reaction equation
[CH3:1][O:2][C:3](=[O:20])[CH:4]([C:11]1[CH:19]=[CH:18][C:14]([C:15]([OH:17])=O)=[CH:13][CH:12]=1)[CH2:5][NH:6][C:7]([NH:9][CH3:10])=[O:8].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[NH2:42][C:43]1[CH:48]=[C:47]([C:49]2[CH:53]=[CH:52][S:51][CH:50]=2)[CH:46]=[CH:45][C:44]=1[NH:54][C:55](=[O:61])[O:56][C:57]([CH3:60])([CH3:59])[CH3:58]>CN(C=O)C>[C:57]([O:56][C:55]([NH:54][C:44]1[CH:45]=[CH:46][C:47]([C:49]2[CH:53]=[CH:52][S:51][CH:50]=2)=[CH:48][C:43]=1[NH:42][C:15]([C:14]1[CH:13]=[CH:12][C:11]([CH:4]([CH2:5][NH:6][C:7]([NH:9][CH3:10])=[O:8])[C:3]([O:2][CH3:1])=[O:20])=[CH:19][CH:18]=1)=[O:17])=[O:61])([CH3:60])([CH3:58])[CH3:59]

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 576118884-[2-Methoxy-1-({[(methylamino)carbonyl]amino}methyl)-2-oxoethyl]benzoic acidHCID 57717476Tert-butyl [2-amino-4-(3-thienyl)phenyl]carbamate

Product 1

HCID 57611887Methyl 2-[4-({[2-[(tert-butoxycarbonyl)amino]-5-(3-thienyl)phenyl]amino}carbonyl)phenyl]-3-{[(methylamino)carbonyl]-amino}propanoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-[2-Methoxy-1-({[(methylamino)carbonyl]amino}-methyl)-2-oxoethyl]benzoic acid (350 mg, 1.25 mmol), EDCI (312 mg, 1.63 mmol), and HOBT (220 mg, 1.63 mmol) were combined in DMF (15 mL) and stirred for 10 minutes before adding tert-butyl [2-amino-4-(3-thienyl)phenyl]carbamate (398 mg, 1.37 mmol). The reaction was then stirred at 55° C. for 24 h. The solvent was evaporated, and the resulting residue was dissolved in EtOAc, washed (water, brine), dried (MgSO4), and concentrated. Flash chromatography on silica (0-5% MeOH/CH2Cl2) afforded methyl 2-[4-({[2-[(tert-butoxycarbonyl)amino]-5-(3-thienyl)phenyl]amino}carbonyl)phenyl]-3-{[(methylamino)carbonyl]amino}propanoate as a white solid. MS (ESI) calcd [M+H]+ 553.2, found 553.2.

Workup

  1. stirringThe reaction was then stirred at 55° C. for 24 h
  2. customThe solvent was evaporated
  3. dissolutionthe resulting residue was dissolved in EtOAc
  4. washwashed (water, brine)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-db519cf7c67d4242a145bcd25195c81b
Source dataset
uspto-grants-2012_05
Patent number
US08168658B2

Reaction notes

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