1-Hydroxybenzotriazole → HCID 44231331, compound

HRID 1665644Notes

Reaction equation

HRID 1665644 reaction equation
C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.[C:20]1([C:26]2[N:27]=[C:28]([NH:31][C:32](=[O:37])[CH2:33][C:34]([OH:36])=O)[S:29][CH:30]=2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.CCN=C=NCCCN(C)C.Cl.Cl.[N:51]1([C:57]([C:59]2[CH:64]=[CH:63][CH:62]=[CH:61][C:60]=2[C:65]([F:68])([F:67])[F:66])=[O:58])[CH2:56][CH2:55][NH:54][CH2:53][CH2:52]1>CN(C=O)C.O>[O:36]=[C:34]([N:54]1[CH2:55][CH2:56][N:51]([C:57](=[O:58])[C:59]2[CH:64]=[CH:63][CH:62]=[CH:61][C:60]=2[C:65]([F:68])([F:66])[F:67])[CH2:52][CH2:53]1)[CH2:33][C:32]([NH:31][C:28]1[S:29][CH:30]=[C:26]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[N:27]=1)=[O:37]

Participants

8

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 167337831-(2-Trifluoromethylbenzoyl)piperazine hydrochlorideHCID 57875803HCID 57875803, compound

Product 1

HCID 44231331HCID 44231331, compoundYield 14.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
10 °C

Procedure

HOBt (38 mg, 0.29 mmol) and DIEA (111 mg, 0.85 mmol) were added to a stirred solution of N-(4-phenyl-thiazol-2-yl)-malonamic acid (75 mg, 0.29 mmol) in DMF (1.5 mL). The reaction mixture was cooled to 10° C. and EDCI.HCl (66 mg, 0.34 mmol) followed by piperazin-1-yl-(2-trifluoromethyl-phenyl)-methanone hydrochloride (92 mg, 0.3 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 sodium bicarbonate and brine solution, dried over Na2SO4 and concentrated to afford 21 mg (13%) of 3-Oxo-N-(4-phenyl-thiazol-2-yl)-3-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-propionamide. LCMS: 503.13 (M+1)+, 97.4%, 1H NMR: (CDCl3): δ 7.85 (d, 2H), 7.74 (d, 1H), 7.6 (m, 2H), 7.4 (td, 2H), 7.33 (m, 2H), 7.15 (d, 1H), 4.02 (m, 2H), 3.7 (m, 4H), 3.52 (m, 2H), 3.24 (m, 2H).

Workup

  1. additionwere added
  2. extractionthe product extracted with ethyl acetate
  3. washThe organic layer was washed with sodium bicarbonate and brine solution
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-5fbe22c0e683408d973a04b08b885627
Source dataset
uspto-grants-2011_10
Patent number
US08039463B2

Reaction notes

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