1-Hydroxybenzotriazole → HCID 57874516, compound

HRID 1093670Notes

Reaction equation

HRID 1093670 reaction equation
[C:1]1([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:6]=[CH:5][C:4]([NH:7][C:8](=[O:13])[CH2:9][C:10]([OH:12])=O)=[CH:3][CH:2]=1.CCN(C(C)C)C(C)C.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.Cl.[Br:52][C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][C:54]=1[S:59][CH:60]1[CH2:65][CH2:64][NH:63][CH2:62][CH2:61]1>CN(C=O)C.O>[C:1]1([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:2]=[CH:3][C:4]([NH:7][C:8](=[O:13])[CH2:9][C:10]([N:63]2[CH2:62][CH2:61][CH:60]([S:59][C:54]3[CH:55]=[CH:56][CH:57]=[CH:58][C:53]=3[Br:52])[CH2:65][CH2:64]2)=[O:12])=[CH:5][CH:6]=1

Participants

8

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 55049154N-biphenyl-4-yl-malonamic acidHCID 66591387HCID 66591387, compound

Product 1

HCID 57874516HCID 57874516, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of N-biphenyl-4-yl-malonamic acid (0.15 g, 0.00059 mole) in DMF (4 mL) was added DIPEA (0.226 g, 0.00176 mole), HOBt (0.095 g, 0.00071 mole) and EDCI.HCl (0.134 g, 0.00071 mole). After 2 minutes 4-(2-bromo-phenylsulfanyl)-piperidine hydrochloride (0.21 g, 0.00071 mole) was added and the resulting mixture was stirred overnight. The reaction mixture was then diluted with cold water and the resulting precipitate was isolated by filtration. Purification by column chromatography using silica gel 60-120 mesh (60% ethyl acetate in hexane) afforded 0.153 g (51%) of N-biphenyl-4-yl-3-[4-(2-bromo-phenylsulfanyl)-piperidin-1-yl]-3-oxo-propionamide. LC-MS purity: 509.08 (M+1)+, 87.3%, 1H NMR (DMSO-d6): δ 10.2 (s, 1H), 7.82-7.6 (m, 6H), 7.48-7.36 (m, 3H), 7.36-7.28 (m, 1H), 7.22-7.12 (m, 1H), 5.6-5.2 (d, 1H), 4.25 (d, 1H), 3.7 (m, 1H), 3.55 (s, 2H), 2.95 (m, 1H), 2.0 (m, 2H), 1.7-1.5 (m, 1H), 1.5-1.35 (m, 1H).

Workup

  1. customthe resulting precipitate was isolated by filtration
  2. customPurification by column chromatography

Sources & evidence

ORD record
ord-151523ccbe944db49b674cf4ca1b0c75
Source dataset
uspto-grants-2012_03
Patent number
US08129376B2

Reaction notes

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