1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 59553871, compound

HRID 1170876Notes

Reaction equation

HRID 1170876 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][CH:23]=1)[C:5]([N:7]([CH3:20])[C:8]1[N:9]=[C:10]2[CH2:15][CH2:14][CH2:13][CH2:12][N:11]2[C:16]=1[C:17](O)=[O:18])=[O:6].CCN=C=NCCCN(C)C.C1C=NC2N(O)N=NC=2C=1.[CH2:45]([NH2:55])[C:46]1[CH:54]=[CH:53][C:52]2[O:51][CH2:50][O:49][C:48]=2[CH:47]=1>C(Cl)Cl>[O:51]1[C:52]2[CH:53]=[CH:54][C:46]([CH2:45][NH:55][C:17]([C:16]3[N:11]4[CH2:12][CH2:13][CH2:14][CH2:15][C:10]4=[N:9][C:8]=3[N:7]([C:5](=[O:6])[C:4]3[CH:21]=[CH:22][CH:23]=[C:2]([Cl:1])[CH:3]=3)[CH3:20])=[O:18])=[CH:47][C:48]=2[O:49][CH2:50]1

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 75799Benzo-1,3-dioxole-5-methylamineHCID 181649HOAtHCID 57465089HCID 57465089, compound

Product 1

HCID 59553871HCID 59553871, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-[(3-chloro-benzoyl)-methyl-amino]-5,6,7,8-tetrahydro-imidazo[1,2-a]pyridine-3-carboxylic acid (232 mg, 0.70 mmol), EDCI (146.6 mg, 0.76 mmol, 1.1 eq.) and HOAt (9.5 mg, 0.07 mmol, 0.1 eq.) were dissolved in DCM (10 mL). Piperonylamine (96 μL, 0.77 mmol, 1.1 eq.) was then added thereto. The reaction mixture was stirred over night and the solvent was then removed. EtOAc (70 mL) was added thereto and the reaction mixture was washed in succession with 0.5 M KHSO4 in water (70 mL) and saturated aqueous NaHCO3 solution (70 mL). The aqueous phases were extracted with EtOAc (30 mL). The combined organic phases were washed with saturated aqueous NaCl solution (70 mL), dried over sodium sulphate, and the solvent was removed under vacuum. The untreated product was purified by column chromatography (SiO2, DCM→DCM/2% MeOH). 116.8 mg (36%) of the desired product 2-[(3-chloro-benzoyl)-methyl-amino]-5,6,7,8-tetrahydro-imidazo[1,2-a]pyridine-3-carboxylic acid(benzo[1,3]dioxol-5-ylmethyl)-amide were obtained.

Workup

  1. customthe solvent was then removed
  2. additionEtOAc (70 mL) was added
  3. washthe reaction mixture was washed in succession with 0.5 M KHSO4 in water (70 mL) and saturated aqueous NaHCO3 solution (70 mL)
  4. extractionThe aqueous phases were extracted with EtOAc (30 mL)
  5. washThe combined organic phases were washed with saturated aqueous NaCl solution (70 mL)
  6. dry with materialdried over sodium sulphate
  7. customthe solvent was removed under vacuum
  8. customThe untreated product was purified by column chromatography (SiO2, DCM→DCM/2% MeOH)

Sources & evidence

ORD record
ord-b22e368201314d9599efd19fc401011e
Source dataset
uspto-grants-2010_11
Patent number
US07829568B2

Reaction notes

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