1-Hydroxybenzotriazole → HCID 178440813, compound

HRID 1093613Notes

Reaction equation

HRID 1093613 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.[C:52]([C:56]1[CH:61]=[CH:60][CH:59]=[CH:58][C:57]=1[NH:62][CH:63]1[CH2:68][CH2:67][NH:66][CH2:65][CH2:64]1)([CH3:55])([CH3:54])[CH3:53]>CN(C=O)C.O>[C:52]([C:56]1[CH:61]=[CH:60][CH:59]=[CH:58][C:57]=1[NH:62][CH:63]1[CH2:68][CH2:67][N:66]([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])[CH2:65][CH2:64]1)([CH3:55])([CH3:53])[CH3:54]

Participants

8

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 66591489(2-Tert-butyl-phenyl)-piperidin-4-yl-amine dihydrochlorideHCID 178525878HCID 178525878, compound

Product 1

HCID 178440813HCID 178440813, compoundYield 49%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of [(5-phenyl-1H-pyrazole-3-carbonyl)-amino]-acetic acid (0.088 g, 0.00036 mol) in DMF (2 mL) was added DIPEA (0.211 g, 0.0016 mol), HOBt (0.048 g, 0.00036 mol) and EDCI.HCl (0.125 g, 0.000655 mol) at ambient temperature. After 2 minutes (2-tert-butyl-phenyl)-piperidin-4-yl-amine dihydrochloride (0.1 g, 0.00033 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 0.07 g (49%) of 5-phenyl-1H-pyrazole-3-carboxylic acid {2-[4-(2-tert-butyl-phenylamino)-piperidin-1-yl]-2-oxo-ethyl}-amide. LCMS: 460.26 (M+1)+, 89.75%, 1H NMR (DMSO-d6): δ 13.8 (s, 1H), 8.1 (s, 1H), 7.8 (d, 2H), 7.6-7.4 (m, 3H), 7.2-7.0 (m, 3H), 6.8 (d, 1H), 6.6 (t, 1H), 4.3 (d, 1H), 4.2 (d, 2H), 3.9 (m, 2H), 3.7 (s, 1H), 3.2 (t, 1H), 2.8 (t, 1H), 2.0 (t, 3H), 1.4 (s, 9H), 1.0 (bs, 1H).

Workup

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

Sources & evidence

ORD record
ord-44984733f5134152be765ce82427b739
Source dataset
uspto-grants-2012_03
Patent number
US08129376B2

Reaction notes

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