1-Hydroxybenzotriazole → HCID 44231565, compound

HRID 1665673Notes

Reaction equation

HRID 1665673 reaction equation
[CH:1]1[CH:2]=[CH:3][C:4]2N(O)N=N[C:5]=2[CH:6]=1.C[CH2:12][N:13](C(C)C)C(C)C.CCN=C=NCCCN(C)C.Cl.Cl.[N:33]1([CH:39]=[O:40])[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]1.[C:41]1([C:55]2[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=2)[CH:46]=[CH:45][C:44]([NH:47][C:48](=[O:54])[CH:49]([F:53])[C:50]([OH:52])=O)=[CH:43][CH:42]=1>CN(C=O)C.O>[C:41]1([C:55]2[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=2)[CH:42]=[CH:43][C:44]([NH:47][C:48](=[O:54])[CH:49]([F:53])[C:50]([N:36]2[CH2:37][CH2:38][N:33]([C:39](=[O:40])[C:6]3[CH:1]=[CH:2][CH:3]=[C:4]([C:12]#[N:13])[CH:5]=3)[CH2:34][CH2:35]2)=[O:52])=[CH:45][CH:46]=1

Participants

8

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 18946299260252-88-8HCID 57875825HCID 57875825, compound

Product 1

HCID 44231565HCID 44231565, compoundYield 30.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

HOBt (60 mg, 0.43 mmol), DIPEA (141 mg, 1.09 mmol), EDCI.HCl (84 mg, 0.43 mmol), 3-cyano-phenyl)-piperazin-1-yl-methanone hydrochloride (110 mg, 0.439 mmol) were added to a stirred solution of N-biphenyl-4-yl-2-fluoro-malonamic acid (100 mg, 0.36 mmol) in DMF (2.0 mL) and the resulting mixture was stirred at the ambient temperature overnight. The mixture was then diluted with water and the product was extracted with ethyl acetate. The organics were washed with brine and concentrated to afford 51 mg (29.65%) of N-Biphenyl-4-yl-3-[4-(3-cyano-benzoyl)-piperazin-1-yl]-2-fluoro-3-oxo-propionamide. LCMS: 471.18 (M+1)+, 95.1%, 1H NMR (DMSO-d6): δ 8.3 (s, 1H), 7.8-7.3 (m, 13H), 4.3-3.7 (m, 3H), 3.7-3.3 (m, 5H).

Workup

  1. extractionthe product was extracted with ethyl acetate
  2. washThe organics were washed with brine
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-a6fdfe3ca7424d82847cd445a4e4ddc0
Source dataset
uspto-grants-2011_10
Patent number
US08039463B2

Reaction notes

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