Diisopropylcarbodiimide → HCID 44231328, compound

HRID 1665635Notes

Reaction equation

HRID 1665635 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([NH:8][CH3:9])=[O:7])=[CH:4][CH:3]=1.[O:12]=[C:13]([N:18]1[CH2:23][CH2:22][N:21]([C:24](=[O:35])[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[C:31]([F:34])([F:33])[F:32])[CH2:20][CH2:19]1)[CH2:14][C:15](O)=[O:16].CC(C)N=C=NC(C)C>C1COCC1>[CH3:9][NH:8][C:6](=[O:7])[C:5]1[CH:4]=[CH:3][C:2]([NH:1][C:15](=[O:16])[CH2:14][C:13](=[O:12])[N:18]2[CH2:19][CH2:20][N:21]([C:24](=[O:35])[C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[C:31]([F:32])([F:34])[F:33])[CH2:22][CH2:23]2)=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 12734DiisopropylcarbodiimideHCID 2355164-Amino-N-methylbenzamideHCID 578758113-Oxo-3-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-propionic acid

Product 1

HCID 44231328HCID 44231328, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-Amino-N-methyl-benzamide (40 g, 0.3 mol) was added to a stirred solution of 3-oxo-3-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-propionic acid (100 mg, 0.3 mmol) and DIC (50 mg, 0.4 mmol) in THF (2 mL) and the mixture was stirred overnight. The resulting precipitate was filtered and extracted with ethyl acetate. The organic layer was washed with brine solution, dried over Na2SO4 and concentrated. The residue was purified by column chromatography using basic alumina (methanol in chloroform) to afford 56 mg (40%) of N-methyl-4-{3-oxo-3-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-propionylamino}-benzamide. LCMS: 477.17 (M+1)+, 94.5%, 1H NMR: (DMSO-d6): δ 7.8 (m, 2H), 7.6 (m, 4H), 7.4 (m, 1H), 4.0 (m, 2H), 3.8 (m, 4H), 3.6 (m, 3H), 3.2 (m, 2H), 3.0 (d, 3H).

Workup

  1. filtrationThe resulting precipitate was filtered
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine solution
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-184bcc8f83814ac4996baa73f2c2285d
Source dataset
uspto-grants-2011_10
Patent number
US08039463B2

Reaction notes

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