Hydrochloric Acid → N-(2-Amino-2-methylcyclopentyl)-2-(2H-1,2,3-triazol-2-yl)benzamide hydrochloride

HRID 1750511Notes

Reaction equation

HRID 1750511 reaction equation
[N:1]1[N:2]([C:6]2[CH:14]=[CH:13][CH:12]=[CH:11][C:7]=2[C:8]([Cl:10])=[O:9])[N:3]=[CH:4][CH:5]=1.[NH2:15][CH:16]1[CH2:20][CH2:19][CH2:18][C:17]1([NH:22]C(=O)OC(C)(C)C)[CH3:21].CCN(C(C)C)C(C)C.Cl.O1CCOCC1>C(Cl)Cl>[ClH:10].[NH2:22][C:17]1([CH3:21])[CH2:18][CH2:19][CH2:20][CH:16]1[NH:15][C:8](=[O:9])[C:7]1[CH:11]=[CH:12][CH:13]=[CH:14][C:6]=1[N:2]1[N:3]=[CH:4][CH:5]=[N:1]1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 81531DiisopropylethylamineHCID 593960352-(2h-1,2,3-Triazol-2-yl)benzoyl chlorideHCID 84783510tert-Butyl N-(2-amino-1-methylcyclopentyl)carbamate2×

Product 1

HCID 118025536N-(2-Amino-2-methylcyclopentyl)-2-(2H-1,2,3-triazol-2-yl)benzamide hydrochloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(2H-1,2,3-triazol-2-yl)benzoyl chloride (213 mg, 1.03 mmol) (which was prepared from 2-(2H-1,2,3-triazol-2-yl)benzoic acid (CAS number 1001401-62-2; 0.194 g, 1.03 mmol) and thionyl chloride (0.112 ml, 1.541 mmol)) in dry DCM (3.1 ml) was added tert-butyl N-(2-amino-1-methylcyclopentyl)carbamate (Intermediate 24; 200 mg, 0.93 mmol) and DIPEA (489 μl, 2.80 mmol). The reaction was stirred at room temperature for 17 hours and was then partitioned between a saturated solution of sodium bicarbonate and DCM, filtered through a hydrophobic frit and concentrated in vacuo. This was then purified by column chromatography (silica, 0-100% ethyl acetate/petrol). The resulting product was then dissolved in 1,4-dioxane (5 ml) and to this was then added HCl in 1,4-dioxane (4 M, 2.3 ml, 9.33 mmol). The reaction was stirred at room temperature for 1 hour and then concentrated in vacuo, azeotropically distilled with toluene to afford the title compound.

Workup

  1. customwas then partitioned between a saturated solution of sodium bicarbonate and DCM
  2. filtrationfiltered through a hydrophobic frit
  3. concentrationconcentrated in vacuo
  4. customThis was then purified by column chromatography (silica, 0-100% ethyl acetate/petrol)
  5. dissolutionThe resulting product was then dissolved in 1,4-dioxane (5 ml)
  6. stirringThe reaction was stirred at room temperature for 1 hour
  7. concentrationconcentrated in vacuo
  8. distillationazeotropically distilled with toluene

Sources & evidence

ORD record
ord-157ac2b476c94064b2d0ae249b06383a
Source dataset
uspto-grants-2015_10
Patent number
US09156829B2

Reaction notes

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