Dimethylformamide → HCID 44231209, compound

HRID 1665620Notes

Reaction equation

HRID 1665620 reaction equation
[CH:1]1[CH:2]=[CH:3][C:4]2[N:9](O)N=N[C:5]=2[CH:6]=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]([OH:16])=O.C[CH2:36][N:37]=[C:38]=[N:39]CCCN(C)C.Cl.CN(C=[O:51])C>CN(C1C=CN=CC=1)C.O>[O:51]1[CH:36]=[N:37][C:38]([C:1]2[CH:6]=[CH:5][C:4]([NH:9][C:14](=[O:16])[CH2:13][C:12](=[O:11])[N:17]3[CH2:18][CH2:19][N:20]([C:23](=[O:34])[C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[C:30]([F:32])([F:31])[F:33])[CH2:21][CH2:22]3)=[CH:3][CH:2]=2)=[N:39]1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 578758113-Oxo-3-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-propionic acid

Product 1

HCID 44231209HCID 44231209, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolvent

Conditions

Temperature
10 °C

Procedure

HOBt (153 mg, 1.13 mmol) and DMAP (172 mg, 1.4 mmol) were added to a stirred solution of 3-oxo-3-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-propionic acid (325 mg, 9.45 mmol) in DMF (2 mL). The reaction mixture was cooled to 10° C. and EDCI.HCl (217 mg, 1.13 mmol) followed by 4-[1,2,4]oxadiazol-3-yl-phenylamine-2-yl-amine (152 mg, 9.4 mmol) were added. The reaction mixture was stirred at the 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 evaporated. The residue was washed with ether and dried to afford 220 mg (48%) of N-(4-[1,2,4]oxadiazol-3-yl-phenyl)-3-oxo-3-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-propionamide. LCMS: 488.15 (M+1)+, 96.97%. 1H NMR: (CDCl3): δ 10.0 (d, 1H), 8.74 (s, 1H), 8.08 (d, 2H), 7.7 (m, 3H), 7.6 (m, 2H), 7.34 (d, 1H), 4.02 (m, 2H), 3.7 (m, 3H), 3.5 (m, 4H), 3.26 (m, 2H).

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. customevaporated
  6. washThe residue was washed with ether
  7. customdried

Sources & evidence

ORD record
ord-359073bee6854683900b446618a6eda5
Source dataset
uspto-grants-2011_10
Patent number
US08039463B2

Reaction notes

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