1-Hydroxybenzotriazole → HCID 178432687, compound

HRID 1093742Notes

Reaction equation

HRID 1093742 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][C:52]1[C:57]([O:58][CH:59]2[CH2:64][CH2:63][NH:62][CH2:61][CH2:60]2)=[CH:56][CH:55]=[CH:54][N:53]=1>CN(C=O)C.O>[CH3:51][C:52]1[C:57]([O:58][CH:59]2[CH2:64][CH2:63][N:62]([C:25](=[O:27])[CH2:24][NH:23][C:21]([C:18]3[CH:17]=[C:16]([C:10]4[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=4)[NH:20][N:19]=3)=[O:22])[CH2:61][CH2:60]2)=[CH:56][CH:55]=[CH:54][N:53]=1

Participants

8

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 66591407HCID 66591407, compoundHCID 178525878HCID 178525878, compound

Product 1

HCID 178432687HCID 178432687, compoundYield 47.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

DIPEA (193 mg, 1.5 mmol) was added to a stirred solution of [(5-phenyl-1H-pyrazole-3-carbonyl)-amino]-acetic acid (127 mg, 0.5 mmol) in DMF (2 mL) followed by HOBt (67 mg, 0.5 mmol) and EDCI.HCl (105 mg, 0.55 mmol). After 2 minutes 2-methyl-3-(piperidin-4-yloxy)-pyridine hydrochloride (100 mg, 0.5 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, and the solid was collected. Purification of the solid by washing with 10% MeOH in CHCl3 afforded 95 mg (47.5% Yield) of 5-phenyl-1H-pyrazole-3-carboxylic acid {2-[4-(2-methyl-pyridin-3-yloxy)-piperidin-1-yl]-2-oxo-ethyl}-amide. LC/MS [M+H]+: 420, 96.7%. 1H NMR (300 MHz, DMSO-d6): δ 8.3 (m, 1H), 8.2 (b, 1H), 8.0 (m, 1H), 7.8 (m, 2H), 7.6 (m, 1H), 7.5 (m, 2H), 7.4 (m, 1H), 7.2 (b, 1H), 4.9 (m, 1H), 4.2 (m, 2H), 3.8 (m, 2H), 3.5 (m, 2H), 2.5 (m, 3H), 2.0 (m, 2H), 1.8 (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-3093619f16d441feb8a2f5fbe1905c68
Source dataset
uspto-grants-2012_03
Patent number
US08129376B2

Reaction notes

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