1-Hydroxybenzotriazole → HCID 178523530, compound

HRID 1093606Notes

Reaction equation

HRID 1093606 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.[F:51][C:52]([F:67])([F:66])[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>[O:18]=[C:16]([N:63]1[CH2:62][CH2:61][CH:60]([S:59][C:54]2[CH:55]=[CH:56][CH:57]=[CH:58][C:53]=2[C:52]([F:66])([F:51])[F:67])[CH2:65][CH2:64]1)[CH2:15][NH:14][C:12]([C:9]1[CH:8]=[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[NH:11][N:10]=1)=[O:13]

Participants

8

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 66591366HCID 66591366, compoundHCID 178525878HCID 178525878, compound

Product 1

HCID 178523530HCID 178523530, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of [(5-Phenyl-1H-pyrazole-3-carbonyl)-amino]-acetic acid (0.05 g, 0.00018 mol) in DMF (1 mL) was added DIPEA (0.0689 g, 0.00053 mol), HOBt (0.028 g, 0.00021 mol) and EDCI.HCl (0.0407 g, 0.00021 mol) at ambient temperature. After 2 minutes 4-(2-trifluoromethyl-phenylsulfanyl)-piperidine hydrochloride (0.063 g, 0.00021 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 0.068 g (78%) of 5-phenyl-1H-pyrazole-3-carboxylic acid {2-oxo-2-[4-(2-trifluoromethyl-phenylsulfanyl)-piperidin-1-yl]-ethyl}-amide. LCMS: 489.15 (M+1)+, 94.5%, 1H NMR (DMSO-d6): δ 13.8 (s, 1H), 8.0 (s, 1H), 7.8 (m, 4H), 7.65 (t, 1H), 7.5-7.3 (m, 4H), 7.1 (s, 1H), 4.3-4.05 (m, 3H), 3.9-3.6 (m, 2H), 3.2 (m, 1H), 2.9 (m, 1H), 1.9 (m, 2H), 1.6 (m, 1H), 1.4 (m, 1H).

Workup

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

Sources & evidence

ORD record
ord-fa4b82f33db347749dfb6b0121f283d4
Source dataset
uspto-grants-2012_03
Patent number
US08129376B2

Reaction notes

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