1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 59128627, compound

HRID 1991004Notes

Reaction equation

HRID 1991004 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][C:3]=1[C:11]1[C:22](=[O:23])[N:21]([CH3:24])[C:14]2[N:15]=[C:16]([S:19][CH3:20])[N:17]=[CH:18][C:13]=2[CH:12]=1.[CH:25]1([NH2:28])[CH2:27][CH2:26]1.CCN=C=NCCCN(C)C>CN(C=O)C>[CH:25]1([NH:28][C:6](=[O:8])[C:5]2[CH:9]=[CH:10][C:2]([CH3:1])=[C:3]([C:11]3[C:22](=[O:23])[N:21]([CH3:24])[C:14]4[N:15]=[C:16]([S:19][CH3:20])[N:17]=[CH:18][C:13]=4[CH:12]=3)[CH:4]=2)[CH2:27][CH2:26]1

Participants

5

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 69828CyclopropylamineHCID 59128649HCID 59128649, compound

Product 1

HCID 59128627HCID 59128627, compoundYield 14.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Methyl-3-(8-methyl-2-methylsulfanyl-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidin-6-yl)-benzoic acid (150 mg, 0.44 mmol) was taken up in 2 mL DMF, and cyclopropylamine (50 mg, 0.88 mmol) was added, followed by EDCI (1.2 g, 0.527 mmol, 1.2 eq.). The reaction mixture was stirred at room temperature for 90 minutes, then partitioned between water and EtOAc. The organic layer was washed with brine, dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by preparative thin layer chromatography (EtOAc/hexanes 1:1) to give 25 mg of N-cyclopropyl-4-methyl-3-(8-methyl-2-methylsulfanyl-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidin-6-yl)-benzamide MS (M+H)=381.

Workup

  1. custompartitioned between water and EtOAc
  2. washThe organic layer was washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by preparative thin layer chromatography (EtOAc/hexanes 1:1)

Sources & evidence

ORD record
ord-ffde95d4be264a29ba8a159eb2153342
Source dataset
uspto-grants-2010_01
Patent number
US07645764B2

Reaction notes

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