Diisopropylethylamine → Biphenyl-4-carboxylic acid {2-[4-(2-bromo-phenylamino)-piperidin-1-yl]-2-oxo-ethyl}-amide

HRID 1093573Notes

Reaction equation

HRID 1093573 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]([C:7]([NH:9][CH2:10][C:11]([OH:13])=O)=[O:8])=[CH:3][CH:2]=1.CCN(C(C)C)C(C)C.CCN=C=NCCCN(C)C.Cl.Cl.Cl.[Br:43][C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][C:45]=1[NH:50][CH:51]1[CH2:56][CH2:55][NH:54][CH2:53][CH2:52]1>CN(C=O)C.O>[Br:43][C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][C:45]=1[NH:50][CH:51]1[CH2:56][CH2:55][N:54]([C:11](=[O:13])[CH2:10][NH:9][C:7]([C:4]2[CH:3]=[CH:2][C:1]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[CH:6][CH:5]=2)=[O:8])[CH2:53][CH2:52]1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 2629432-((4-Phenylphenyl)formamido)acetic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 66545672N-(2-Bromophenyl)piperidin-4-amine dihydrochloride

Product 1

HCID 44235272Biphenyl-4-carboxylic acid {2-[4-(2-bromo-phenylamino)-piperidin-1-yl]-2-oxo-ethyl}-amideYield 46.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of [(biphenyl-4-carbonyl)-amino]-acetic acid (0.075 g, 0.00029 mol) in DMF (2 mL), was added DIPEA (0.1139 g, 0.00088 mol) HOBt (0.0398 g, 0.00029 mol) and EDCI.HCl (0.06758 g, 0.00035 mol) at ambient temperature. After 2 minutes (2-bromo-phenyl)-piperidin-4-yl-amine dihydrochloride (0.09639 g, 0.00029 mol) was added and the resulting mixture was stirred at the same temperature for overnight. The reaction mixture was diluted with cold water and the resulting precipitate was isolated by filtration, washed with hexane followed by ether and dried to afford 0.067 g (46%) of biphenyl-4-carboxylic acid {2-[4-(2-bromo-phenylamino)-piperidin-1-yl]-2-oxo-ethyl}-amide. LCMS: 492.0 (M+1)+, 90.08%, 1H NMR (DMSO-d6): δ 8.62 (t, 1H), 7.94 (d, 2H), 7.79 (m, 4H), 7.5 (t, 2H), 7.4 (t, 2H), 7.2 (t, 1H), 6.84 (d, 1H), 6.57 (d, 1H), 4.6 (d, 1H), 4.3 (d, 1H), 4.2 (d, 2H), 3.9 (d, 1H), 3.6 (d, 1H), 2.7 (t, 1H), 1.9 (bs, 2H), 1.5-1.2 (m, 3H).

Workup

  1. customthe resulting precipitate was isolated by filtration
  2. washwashed with hexane
  3. customdried

Sources & evidence

ORD record
ord-521eac9bfb624ffcb739b68eca129b8c
Source dataset
uspto-grants-2012_03
Patent number
US08129376B2

Reaction notes

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