1-Hydroxybenzotriazole → HCID 44231210, compound

HRID 1665624Notes

Reaction equation

HRID 1665624 reaction equation
C1C=CC2N(O)N=NC=2C=1.[O:11]=[C:12]([N:17]1[CH2:22][CH2:21][N:20]([C:23](=[O:34])[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[C:30]([F:33])([F:32])[F:31])[CH2:19][CH2:18]1)[CH2:13][C:14](O)=[O:15].CCN=C=NCCCN(C)C.Cl.[CH3:47][C:48]1[O:52][C:51]([C:53]2[CH:58]=[CH:57][C:56]([NH2:59])=[CH:55][CH:54]=2)=[N:50][N:49]=1>CN(C1C=CN=CC=1)C.CN(C=O)C.O>[CH3:47][C:48]1[O:52][C:51]([C:53]2[CH:58]=[CH:57][C:56]([NH:59][C:14](=[O:15])[CH2:13][C:12](=[O:11])[N:17]3[CH2:22][CH2:21][N:20]([C:23](=[O:34])[C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[C:30]([F:31])([F:32])[F:33])[CH2:19][CH2:18]3)=[CH:55][CH:54]=2)=[N:50][N:49]=1

Participants

8

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 195422444-(5-Methyl-1,3,4-oxadiazol-2-yl)anilineHCID 578758113-Oxo-3-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-propionic acid

Product 1

HCID 44231210HCID 44231210, compoundYield 20%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
10 °C

Procedure

HOBt (72 mg, 0.53 mmol) and DMAP (81 mg, 0.66 mmol) were added to a stirred solution of 3-oxo-3-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-propionic acid (150 mg, 0.44 mmol) in DMF (2 mL). The reaction mixture was cooled to 10° C. and EDCI.HCl (102 mg, 0.53 mmol) followed by 4-(5-methyl-[1,3,4]oxadiazol-2-yl)-phenylamine (77 mg, 0.44 mmol) were added. The reaction mixture was stirred at room temperature overnight then diluted with water and the product extracted with ethyl acetate. The organics were washed with brine solution, dried over Na2SO4 and concentrated. The residue was purified by column chromatography using basic alumina (80% ethyl acetate in hexane) to afford 40 mg (20%) of N-[4-(5-methyl-[1,3,4]oxadiazol-2-yl)-phenyl]-3-oxo-3-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-propionamide. LCMS: 502.17 (M+1)+, 94.56%, 1H NMR: (DMSO-d6): δ 10.5 (d, 1H), 7.92 (m, 2H), 7.8 (m, 4H), 7.68 (t, 1H), 7.56 (m, 1H), 3.68 (m, 7H), 3.44 (m, 2H), 3.18 (m, 1H), 3.08 (m, 1H), 2.58 (s, 3H).

Workup

  1. additionwere added
  2. extractionthe product extracted with ethyl acetate
  3. washThe organics were 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-6d5f6d6b569647059fd178d8bc8c464d
Source dataset
uspto-grants-2011_10
Patent number
US08039463B2

Reaction notes

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