1-Hydroxybenzotriazole → HCID 178428400, compound

HRID 1093747Notes

Reaction equation

HRID 1093747 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[CH:57]=[CH:56][N:55]=[CH:54][C:53]=1[O:58][CH:59]1[CH2:64][CH2:63][NH:62][CH2:61][CH2:60]1>CN(C=O)C.O>[CH3:51][C:52]1[CH:57]=[CH:56][N:55]=[CH:54][C:53]=1[O:58][CH:59]1[CH2:64][CH2:63][N:62]([C:25](=[O:27])[CH2:24][NH:23][C:21]([C:18]2[CH:17]=[C:16]([C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=3)[NH:20][N:19]=2)=[O:22])[CH2:61][CH2:60]1

Participants

8

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 66591714HCID 66591714, compoundHCID 178525878HCID 178525878, compound

Product 1

HCID 178428400HCID 178428400, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

DIPEA (154 mg, 1.4 mmol) was added to a stirred solution of [(5-phenyl-1H-pyrazole-3-carbonyl)-amino]-acetic acid (107 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-methyl-3-(piperidin-4-yloxy)-pyridine hydrochloride (100 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. Purification of the solid by washing with 10% MeOH in CHCl3 afforded 106 mg (66% Yield) of 5-phenyl-1H-pyrazole-3-carboxylic acid {2-[4-(4-methyl-pyridin-3-yloxy)-piperidin-1-yl]-2-oxo-ethyl}-amide. LC/MS [M+H]+: 420, 98.9%. 1H NMR (300 MHz, DMSO-d6): δ 14.0 (b, 1H), 8.6 (s, 1H), 8.4 (d, 1H), 8.2 (b, 1H), 7.8 (m, 3H), 7.5 (m, 2H), 7.4 (m, 1H), 7.2 (s, 1H), 4.9 (m, 1H), 4.2 (m, 2H), 3.8 (m, 2H), 3.5 (m, 2H), 2.4 (s, 3H), 2.0 (m, 2H), 1.7 (m, 2H).

Workup

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

Sources & evidence

ORD record
ord-b0181e1bd014485eb789863772323e1b
Source dataset
uspto-grants-2012_03
Patent number
US08129376B2

Reaction notes

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