1-Hydroxybenzotriazole → HCID 178425687, compound

HRID 1093741Notes

Reaction equation

HRID 1093741 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.[C:51]1([CH3:64])[CH:56]=[CH:55][CH:54]=[C:53]([O:57][CH:58]2[CH2:63][CH2:62][NH:61][CH2:60][CH2:59]2)[CH:52]=1>CN(C=O)C.O>[O:27]=[C:25]([N:61]1[CH2:62][CH2:63][CH:58]([O:57][C:53]2[CH:52]=[C:51]([CH3:64])[CH:56]=[CH:55][CH:54]=2)[CH2:59][CH2:60]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 171967294-(3-Methylphenoxy)piperidine--hydrogen chloride (1/1)HCID 178525878HCID 178525878, compound

Product 1

HCID 178425687HCID 178425687, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

DIPEA (155 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 mL) followed by HOBt (54 mg, 0.4 mmol) and EDCI.HCl (84 mg, 0.44 mmol). After 2 minutes 4-m-tolyloxy-piperidine hydrochloride (107 mg, 0.4 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 collected. The solid was purified by washing with 10% MeOH in CHCl3 to afford 92 mg (56% Yield) 5-phenyl-1H-pyrazole-3-carboxylic acid [2-oxo-2-(4-m-tolyloxy-piperidin-1-yl)-ethyl]-amide. LC/MS [M+H]+: 419, 95.4%. 1H NMR (300 MHz, DMSO-d6): δ13.8 (m, 1H), 8.6 (m, 1H), 8.0 (m, 2H), 7.8 (m, 2H), 7.4 (m, 4H), 7.2 (m, 2H), 6.8 (m, 3H), 4.6 (m, 1H), 4.2 (m, 2H), 3.8 (m, 1H), 3.6 (m, 1H), 3.4 (m, 1H), 3.3 (m, 1H), 2.3 (s, 3H), 2.0 (m, 2H), 1.6 (m, 2H).

Workup

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

Sources & evidence

ORD record
ord-eaebbd0035c84f3fb28044118436873f
Source dataset
uspto-grants-2012_03
Patent number
US08129376B2

Reaction notes

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