1-Hydroxybenzotriazole → HCID 178425122, compound

HRID 1093612Notes

Reaction equation

HRID 1093612 reaction equation
[C:1]1([C:7]2[NH:11][N:10]=[C:9]([C:12]([NH:14][CH2:15][C:16]([OH:18])=O)=[O:13])[CH:8]=2)[CH:6]=[CH:5][CH:4]=[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.Cl.[CH3:52][C:53]1[CH:58]=[CH:57][C:56]([CH3:59])=[CH:55][C:54]=1[NH:60][CH:61]1[CH2:66][CH2:65][NH:64][CH2:63][CH2:62]1>CN(C=O)C.O>[CH3:52][C:53]1[CH:58]=[CH:57][C:56]([CH3:59])=[CH:55][C:54]=1[NH:60][CH:61]1[CH2:66][CH2:65][N:64]([C:16](=[O:18])[CH2:15][NH:14][C:12]([C:9]2[CH:8]=[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[NH:11][N:10]=2)=[O:13])[CH2:63][CH2:62]1

Participants

8

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 66591423(2,5-Dimethyl-phenyl)-piperidin-4-yl-amine dihydrochlorideHCID 178525878HCID 178525878, compound

Product 1

HCID 178425122HCID 178425122, compoundYield 77.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of [(5-phenyl-1H-pyrazole-3-carbonyl)-amino]-acetic acid (0.097 g, 0.00040 mol) in DMF (1 mL) was added DIPEA (0.233 g, 0.00180 mol), HOBt (0.053 g, 0.00040 mol) and EDCI.HCl (0.138 g, 0.00072 mol) at ambient temperature. After 2 minutes (2,5-dimethyl-phenyl)-piperidin-4-yl-amine dihydrochloride (0.1 g, 0.00036 mol) was added and the resulting mixture was stirred overnight. The reaction mixture was then diluted with cold water. The resulting precipitate was isolated by filtration and dried to afford 0.12 g (77%) of 5-phenyl-1H-pyrazole-3-carboxylic acid {2-[4-(2,5-dimethyl-phenylamino)-piperidin-1-yl]-2-oxo-ethyl}-amide. LCMS: 432.23 (M+1)+, 96.91%, 1H NMR (DMSO-d6): δ 8.1 (s, 1H), 7.8 (d, 2H), 7.5 (t, 2H), 7.4 (t, 1H), 7.1 (s, 1H), 6.8 (d, 1H), 6.5 (s, 1H), 6.3 (d, 1H), 4.4 (d, 2H), 4.2 (bs, 2H), 3.9 (d, 1H), 3.6 (bs, 1H), 3.2 (t, 1H), 2.8 (t, 1H), 2.2 (s, 3H), 2.0 (s, 3H), 1.9 (d, 1H), 1.5 (d, 1H), 1.3 (d, 1H).

Workup

  1. customThe resulting precipitate was isolated by filtration
  2. customdried

Sources & evidence

ORD record
ord-7993a548539a402180da236f61e3c58c
Source dataset
uspto-grants-2012_03
Patent number
US08129376B2

Reaction notes

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