1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 44231801, compound

HRID 1665699Notes

Reaction equation

HRID 1665699 reaction equation
CCN(C(C)C)C(C)C.[C:10]1([C:16]2[CH:17]=[CH:18][C:19]([NH:22][C:23](=[O:28])[CH2:24][C:25]([OH:27])=O)=[N:20][CH:21]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.Cl.[N:51]1([C:57]([C:59]2[CH:64]=[C:63]([F:65])[C:62]([F:66])=[C:61]([F:67])[CH:60]=2)=[O:58])[CH2:56][CH2:55][NH:54][CH2:53][CH2:52]1>CN(C=O)C.O>[O:27]=[C:25]([N:54]1[CH2:55][CH2:56][N:51]([C:57](=[O:58])[C:59]2[CH:64]=[C:63]([F:65])[C:62]([F:66])=[C:61]([F:67])[CH:60]=2)[CH2:52][CH2:53]1)[CH2:24][C:23]([NH:22][C:19]1[CH:18]=[CH:17][C:16]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)=[CH:21][N:20]=1)=[O:28]

Participants

8

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 66625657HCID 66625657, compoundHCID 66625674HCID 66625674, compound

Product 1

HCID 44231801HCID 44231801, compoundYield 15.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

DIPEA (453 mg, 3.51 mmol) was added to N-(5-phenyl-pyridin-2-yl)-malonamic acid (300 mg, 1.17 mmol), which was prepared following the synthetic route described in method II, in DMF (3 mL) followed by EDCI (336 mg, 1.75 mmol) and HOBT (189 mg, 1.4 mmol). After 2 minutes, piperazin-1-yl-(3,4,5-trifluoro-phenyl)-methanone hydrochloride (328 mg, 1.17 mmol) was added and stirring was continued at room temperature overnight. Cold water was then added and extracted with ethyl acetate. The organic layer was washed with brine, dried over Na2SO4, and concentrated under reduced pressure. Purification by preparative HPLC afforded 85 mg (15% yield) of 3-oxo-N-(5-phenyl-pyridin-2-yl)-3-[4-(3,4,5-trifluoro-benzoyl)-piperazin-1-yl]-propionamide. LC/S [M+H]+: 483.16, 97.03%. 1H NMR (300 MHz, DMSO-d6): δ 10.7 (s, 1H), 8.7 (s, 1H), 8.1 (s, 2H), 7.7 (d, 2H), 7.5 (m, 4H), 7.4 (m, 1H), 3.7-3.1 (bs, 2H), 3.6-3.2 (m, 8H).

Workup

  1. customwas prepared
  2. waitwas continued at room temperature overnight
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customPurification by preparative HPLC

Sources & evidence

ORD record
ord-f2ad581035b44a6e98cb71a28bfb9c55
Source dataset
uspto-grants-2011_10
Patent number
US08039463B2

Reaction notes

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