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1-Hydroxybenzotriazole → HCID 178425687, compound

HRID 1093741
Notes
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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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 178425687
HCID 178425687, compound
Yield 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
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08129376B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes