1-Hydroxybenzotriazole → HCID 86634608, compound

HRID 1665647Notes

Reaction equation

HRID 1665647 reaction equation
C1C=CC2N(O)N=[N:7]C=2C=1.[O:11]=[C:12]([N:17]1[CH2:22][CH2:21][N:20]([C:23](=[O:33])[C:24]2[CH:29]=[C:28]([F:30])[C:27]([F:31])=[C:26]([F:32])[CH:25]=2)[CH2:19][CH2:18]1)[CH2:13][C:14](O)=[O:15].CCN=C=NCCCN(C)C.Cl.O1C=NC(C2C=CC(N)=CC=2)=N1>CN(C1C=CN=CC=1)C.CN(C=O)C.O>[O:11]=[C:12]([N:17]1[CH2:22][CH2:21][N:20]([C:23](=[O:33])[C:24]2[CH:29]=[C:28]([F:30])[C:27]([F:31])=[C:26]([F:32])[CH:25]=2)[CH2:19][CH2:18]1)[CH2:13][C:14]([NH2:7])=[O:15]

Participants

8

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 214837044-(1,2,4-Oxadiazol-3-yl)anilineHCID 57875813HCID 57875813, compound

Product 1

HCID 86634608HCID 86634608, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
10 °C

Procedure

HOBt (49 mg, 0.36 mmol) and DMAP (55 mg, 0.45 mmol) were added to a stirred solution of 3-oxo-3-[4-(3,4,5-trifluoro-benzoyl)-piperazin-1-yl]-propionic acid (100 mg, 0.3 mmol) in DMF (2 mL). The reaction mixture was cooled to 10° C. and EDCI.HCl (69 mg, 0.36 mmol) followed by 4-[1,2,4]-oxadiazol-3-yl-phenylamine (53 mg, 0.33 mmol) were added. The reaction mixture was stirred at room temperature overnight then diluted with water and the product 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 silica 60-120 mesh (30% ethyl acetate in hexane) to afford 15 mg (11%) of N-(4-[1,2, and 4]oxadiazol-3-yl-phenyl)-3-oxo-3-[4-(3,4,5-trifluoro-benzoyl)-piperazin-1-yl]-propionamide. LCMS: 474.13 (M+1)+, 98.2%, 1H NMR: (DMSO-d6): δ 10.5 (s, 1H), 9.7 (s, 1H), 8.0 (d, 2H), 7.8 (d, 2H), 7.5 (t, 2H), 3.6 (m, 10H).

Workup

  1. additionwere added
  2. extractionthe product extracted 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-1e716230d05c4ab2a2cf33c6cf3448d7
Source dataset
uspto-grants-2011_10
Patent number
US08039463B2

Reaction notes

Loading…