1-Hydroxybenzotriazole → HCID 178504712, compound

HRID 1093754Notes

Reaction equation

HRID 1093754 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.Cl.[CH3:51][S:52]([C:55]1[CH:67]=[CH:66][CH:65]=[CH:64][C:56]=1[O:57][CH:58]1[CH2:63][CH2:62][NH:61][CH2:60][CH2:59]1)(=[O:54])=[O:53]>CN(C=O)C.O>[CH3:51][S:52]([C:55]1[CH:67]=[CH:66][CH:65]=[CH:64][C:56]=1[O:57][CH:58]1[CH2:59][CH2:60][N:61]([C:25](=[O:27])[CH2:24][NH:23][C:21]([C:18]2[CH:17]=[C:16]([C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=3)[NH:20][N:19]=2)=[O:22])[CH2:62][CH2:63]1)(=[O:54])=[O:53]

Participants

8

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 665924674-(2-(Methylsulfonyl)phenoxy)piperidine hydrochlorideHCID 178525878HCID 178525878, compound

Product 1

HCID 178504712HCID 178504712, compoundYield 35.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

DIPEA (63 mg, 0.48 mmol) was added to a stirred solution of [(5-phenyl-1H-pyrazole-3-carbonyl)-amino]-acetic acid (40 mg, 0.163 mmol) in DMF (1 mL) followed by HOBt (26 mg, 0.195 mmol) and EDCI.HCl (37 mg, 0.195 mmol). After 2 minutes 4-(2-methanesulfonyl-phenoxy)-piperidine hydrochloride (57 mg, 0.195 mmol) was added to the reaction mixture and stirring was continued at ambient temperature overnight. The reaction mixture was diluted with cold water and extracted with ethyl acetate. The ethyl acetate was washed with brine solution, dried over sodium sulfate and concentrated under reduced pressure The residue was purified by preparative HPLC to afford 28 mg (26.66% Yield) of 5-phenyl-1H-pyrazole-3-carboxylic acid {2-[4-(2-methanesulfonyl-phenoxy)-piperidin-1-yl]-2-oxo-ethyl}-amide. LC/MS [M+H]+: 483, 98.59%. 1H NMR (300 MHz, CDCl3): δ 8.8 (bs, 1H), 8.0 (m, 1H), 7.7-7.6 (d, 2H), 7.6-7.5 (m, 1H), 7.5-7.3 (m, 3H), 7.2-7.0 (m, 3H), 5.1-4.9 (m, 3H), 4.6-4.5 (dd, 1H), 4.2-4.1 (m, 2H), 3.9-3.4 (m, 3H), 3.2 (s, 3H), 2.1-1.9 (m, 4H).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate was washed with brine solution
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure The residue
  5. customwas purified by preparative HPLC

Sources & evidence

ORD record
ord-dcf236c2380144ad98c040d74e76ee4c
Source dataset
uspto-grants-2012_03
Patent number
US08129376B2

Reaction notes

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