1-Hydroxybenzotriazole → HCID 178523491, compound

HRID 1093815Notes

Reaction equation

HRID 1093815 reaction equation
CCN(C(C)C)C(C)C.[C:10]1([C:16]2[NH:20][N:19]=[C:18]([C:21]([NH:23][CH2:24][C:25]([OH:27])=O)=[O:22])[CH:17]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.FC(F)(F)C(O)=O.[F:57][C:58]([F:73])([F:72])[C:59]1[CH:71]=[CH:70][CH:69]=[CH:68][C:60]=1[O:61][CH:62]1[CH2:67][CH2:66][NH:65][CH2:64][CH2:63]1>CN(C=O)C.O>[O:27]=[C:25]([N:65]1[CH2:64][CH2:63][CH:62]([O:61][C:60]2[CH:68]=[CH:69][CH:70]=[CH:71][C:59]=2[C:58]([F:57])([F:72])[F:73])[CH2:67][CH2:66]1)[CH2:24][NH:23][C:21]([C:18]1[CH:17]=[C:16]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[NH:20][N:19]=1)=[O:22]

Participants

8

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 866346354-(2-Trifluoromethyl-phenoxy)-piperidine trifluoracetateHCID 178525878HCID 178525878, compound

Product 1

HCID 178523491HCID 178523491, compoundYield 58.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

DIPEA (154 mg, 1.2 mmol) was added to a stirred solution of [(5-phenyl-1H-pyrazole-3-carbonyl)-amino]-acetic acid (100 mg, 0.4 mmol) in DMF (2.0 mL) followed by HOBt (60 mg, 0.49 mmol) and EDCI.HCl (93 mg, 0.49 mmol). After 2 minutes of stirring, 4-(2-trifluoromethyl-phenoxy)-piperidine trifluoroacetate (167 mg, 0.49 mmol) (prepared according to Step 1 and 5 of the General Scheme) was added and stirring was continued at ambient temperature overnight. The reaction mixture was diluted with water, extracted with ethylacetate, washed with brine and concentrated to afford 111 mg (57.81% Yield) of 5-phenyl-1H-pyrazole-3-carboxylic acid {2-oxo-2-[4-(2-trifluoromethyl-phenoxy)-piperidin-1-yl]-ethyl}-amide. LC/MS [M+H]+: 473.17, 97.38%, 1H NMR (300 MHz, DMSO-d6): δ13.8 (m, 1H), 8.1 (bs, 1H), 7.9-7.3 (m, 8H), 7.2-7.0 (m, 2H), 4.9 (bs, 1H), 4.2 (m, 2H), 3.8-2.9 (m, 4H), 2.0-1.7 (m, 3H).

Workup

  1. additionwas added
  2. stirringstirring
  3. waitwas continued at ambient temperature overnight
  4. extractionextracted with ethylacetate
  5. washwashed with brine
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-2f425a5334334c5aa616200f2d8d7dff
Source dataset
uspto-grants-2012_03
Patent number
US08129376B2

Reaction notes

Loading…