1-Hydroxybenzotriazole → HCID 178523490, compound

HRID 1093603Notes

Reaction equation

HRID 1093603 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.FC(F)(F)C(O)=O.[Br:57][C:58]1[CH:70]=[CH:69][CH:68]=[CH:67][C:59]=1[O:60][CH:61]1[CH2:66][CH2:65][NH:64][CH2:63][CH2:62]1>CN(C=O)C.O>[Br:57][C:58]1[CH:70]=[CH:69][CH:68]=[CH:67][C:59]=1[O: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 66591525HCID 66591525, compoundHCID 178525878HCID 178525878, compound

Product 1

HCID 178523490HCID 178523490, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of [(5-phenyl-1H-pyrazole-3-carbonyl)-amino]-acetic acid (0.038 g, 0.000135 mol) in DMF (2 mL) was added DIPEA (0.0872 g, 0.00068 mol), HOBt (0.023 g, 0.00017 mol) and EDCI.HCl (0.0325 g, 0.00017 mol) at ambient temperature. After 2 minutes 4-(2-bromophenoxy)-piperidine trifluoroacetate (0.05 g, 0.0001349 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 0.044 g (68%) of 5-phenyl-1H-pyrazole-3-carboxylic acid {2-[4-(2-bromo-phenoxy)-piperidin-1-yl]-2-oxo-ethyl}-amide. LCMS: 483.1 (M+1)+, 99.71%, 1H NMR (DMSO-d6): δ 13.7 (s, 1H), 8.02 (s, 1H), 7.79 (d, 1H), 7.6 (m, 1H), 7.42 (m, 2H), 7.3 (m, 2H), 7.26 (d, 1H), 7.0 (s, 1H), 6.9 (t, 1H), 4.8 (m, 1H), 4.2 (d, 2H), 3.4 (m, 4H), 1.7 (m, 2H), 1.6 (m, 2H).

Workup

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

Sources & evidence

ORD record
ord-40beaae5e84d478f8341323f8ec8f622
Source dataset
uspto-grants-2012_03
Patent number
US08129376B2

Reaction notes

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