Hydrochloric Acid → N-(3-methylpyridin-2-yl)-4-[1-methyl-5-(2H-tetrazol-5-yl)-1H-pyrazol-4-yl]-N-[(3R)-piperidin-3-yl]benzamide

HRID 588398Notes

Reaction equation

HRID 588398 reaction equation
[CH3:1][N:2]1[C:6]([C:7]2[N:8]=[N:9][NH:10][N:11]=2)=[C:5]([C:12]2[CH:40]=[CH:39][C:15]([C:16]([N:18]([C@@H:26]3[CH2:31][CH2:30][CH2:29][N:28](C(OC(C)(C)C)=O)[CH2:27]3)[C:19]3[C:24]([CH3:25])=[CH:23][CH:22]=[CH:21][N:20]=3)=[O:17])=[CH:14][CH:13]=2)[CH:4]=[N:3]1.Cl.O1CCOCC1>CO>[CH3:25][C:24]1[C:19]([N:18]([C@@H:26]2[CH2:31][CH2:30][CH2:29][NH:28][CH2:27]2)[C:16](=[O:17])[C:15]2[CH:39]=[CH:40][C:12]([C:5]3[CH:4]=[N:3][N:2]([CH3:1])[C:6]=3[C:7]3[N:8]=[N:9][NH:10][N:11]=3)=[CH:13][CH:14]=2)=[N:20][CH:21]=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 117661189tert-butyl (3R)-3-(4-(1-methyl-5-(2H-tetrazol-5-yl)-1H-pyrazol-4-yl)-N-(3-methylpyridin-2-yl)benzamido)piperidine-1-carboxylate

Product 1

HCID 86279363N-(3-methylpyridin-2-yl)-4-[1-methyl-5-(2H-tetrazol-5-yl)-1H-pyrazol-4-yl]-N-[(3R)-piperidin-3-yl]benzamideYield 108.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Preparation 25, tert-butyl (3R)-3-(4-(1-methyl-5-(2H-tetrazol-5-yl)-1H-pyrazol-4-yl)-N-(3-methylpyridin-2-yl)benzamido)piperidine-1-carboxylate (100 mg, 0.185 mmol) was dissolved in methanol (0.925 mL). To this was added HCl in dioxane (0.694 mL, 4M solution, 2.78 mmol) at room temperature. The reaction was stirred at room temperature. After 2 h, reaction was concentrated under reduced pressure, and then concentrated with toluene (3×10 mL). The crude material was triturated with EtOAc/MeOH (20:1) and filtered to afford N-(3-methylpyridin-2-yl)-4-[1-methyl-5-(2H-tetrazol-5-yl)-1H-pyrazol-4-yl]-N-[(3R)-piperidin-3-yl]benzamide (89.3 mg, 94%).

Workup

  1. customreaction
  2. concentrationwas concentrated under reduced pressure
  3. concentrationconcentrated with toluene (3×10 mL)
  4. customThe crude material was triturated with EtOAc/MeOH (20:1)
  5. filtrationfiltered

Sources & evidence

ORD record
ord-a9340a25099b499bb0ef5ee5ad0679eb
Source dataset
uspto-grants-2016_01
Patent number
US09227956B2

Reaction notes

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