1-Hydroxybenzotriazole → HCID 178523525, compound

HRID 1093748Notes

Reaction equation

HRID 1093748 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.[NH:51]1[CH2:56][CH2:55][CH:54]([O:57][C:58]2[CH:59]=[N:60][CH:61]=[C:62]([C:64]([F:67])([F:66])[F:65])[CH:63]=2)[CH2:53][CH2:52]1>CN(C=O)C.O>[O:27]=[C:25]([N:51]1[CH2:52][CH2:53][CH:54]([O:57][C:58]2[CH:59]=[N:60][CH:61]=[C:62]([C:64]([F:66])([F:65])[F:67])[CH:63]=2)[CH2:55][CH2:56]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 665925653-(Piperidin-4-yloxy)-5-trifluoromethyl-pyridine hydrochlorideHCID 178525878HCID 178525878, compound

Product 1

HCID 178523525HCID 178523525, compoundYield 47.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

DIPEA (140 mg, 1.1 mmol) was added to a stirred solution of [(5-phenyl-1H-pyrazole-3-carbonyl)-amino]-acetic acid (87 mg, 0.35 mmol) in DMF (2 mL) followed by HOBt (47 mg, 0.35 mmol) and EDCI.HCl (73 mg, 0.38 mmol). After 2 minutes 3-(piperidin-4-yloxy)-5-trifluoromethyl-pyridine hydrochloride (100 mg, 0.35 mmol) (prepared by method used for the synthesis of Intermediate 15) was added to the reaction mixture and stirring was continued at ambient temperature overnight. The reaction mixture was diluted with cold water, the solid was collected. Purification of the solid by washing with 10% MeOH in CHCl3 afforded 76 mg (47.5% Yield) of 5-phenyl-1H-pyrazole-3-carboxylic acid {2-oxo-2-[4-(5-trifluoromethyl-pyridin-3-yloxy)-piperidin-1-yl]-ethyl}-amide. LC/MS [M+H]+: 474, 99%. 1H NMR (300 MHz, DMSO-d6): δ 13.8 (m, 1H), 8.68 (m, 1H), 8.58 (s, 1H), 8.1 (m, 1H), 7.9 (m, 1H), 7.8 (m, 2H), 7.4 (m, 4H), 7.1 (m, 1H), 5.0 (m, 1H), 4.2 (m, 2H), 4.0 (m, 1H), 3.8 (m, 1H), 3.4 (m, 1H), 3.3 (m, 1H), 2.0 (m, 2H), 1.7 (m, 2H).

Workup

  1. additionwas added to the reaction mixture
  2. customthe solid was collected
  3. customPurification of the solid
  4. washby washing with 10% MeOH in CHCl3

Sources & evidence

ORD record
ord-1daa3ddcdcbf4b71ab1fdd8374d1a759
Source dataset
uspto-grants-2012_03
Patent number
US08129376B2

Reaction notes

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