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1-Hydroxybenzotriazole → 5-(2-benzyloxy-phenyl)-1H-pyrazole-3-carboxylic acid {2-[4-(2-chloro-phenoxy)-piperidin-1-yl]-2-oxo-ethyl}-amide

HRID 1093651
Notes
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Reaction equation

HRID 1093651 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1[NH:19][N:18]=[C:17]([C:20]([NH:22][CH2:23][C:24](O)=[O:25])=[O:21])[CH:16]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.[CH:36]1[CH:37]=[CH:38]C2N(O)N=[N:42][C:40]=2[CH:41]=1.CCN=C=NCCCN(C)C.Cl.Cl.[Cl:59][C:60]1[CH:73]=[CH:72][CH:71]=[CH:70][C:61]=1[O:62]NC1CCNCC1>CN(C=O)C.O>[Cl:59][C:60]1[CH:73]=[CH:72][CH:71]=[CH:70][C:61]=1[O:62][CH:36]1[CH2:37][CH2:38][N:42]([C:24](=[O:25])[CH2:23][NH:22][C:20]([C:17]2[CH:16]=[C:15]([C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=3[O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[NH:19][N:18]=2)=[O:21])[CH2:40][CH2:41]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86634616(2-Chlorophenoxy)-piperidin-4-yl-amine hydrochlorideHCID 178525879HCID 178525879, compound

Product 1

HCID 178523494
5-(2-benzyloxy-phenyl)-1H-pyrazole-3-carboxylic acid {2-[4-(2-chloro-phenoxy)-piperidin-1-yl]-2-oxo-ethyl}-amide
Yield 37.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of {[5-(2-benzyloxy-phenyl)-1H-pyrazole-3-carbonyl]-amino}-acetic acid (0.15 g, 0.00039 mol) in DMF (2 mL) was added DIPEA (0.224 g, 0.001736 mol), HOBt (0.065 g, 0.00048 mol) and EDCI.HCl (0.0925 g, 0.000482 mol) at ambient temperature. After 5 minutes (2-chlorophenoxy)-piperidin-4-yl-amine hydrochloride (0.1 g, 0.00041 mol) was added and the resulting mixture was stirred overnight. The reaction mixture was then diluted with cold water and the resulting precipitate was isolated by filtration and dried to afford 0.08 g (33%) of 5-(2-benzyloxy-phenyl)-1H-pyrazole-3-carboxylic acid {2-[4-(2-chloro-phenoxy)-piperidin-1-yl]-2-oxo-ethyl}-amide. LCMS: 544.2 (M+1)+, 99.03%.

Workup

  1. customthe resulting precipitate was isolated by filtration
  2. customdried

Sources & evidence

ORD record
ord-11224c6837624d4680506b0b82ddfeeb
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