1,2-Dichloroethane → HCID 118308085, compound

HRID 1750466Notes

Reaction equation

HRID 1750466 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([N:11]2[N:15]=[CH:14][CH:13]=[N:12]2)=[C:6]([CH:10]=1)[C:7]([OH:9])=O.C(Cl)C[Cl:18].[N:20]1[C:28]2[C:23](=[N:24][CH:25]=[CH:26][CH:27]=2)N(O)N=1.C(N(CC)CC)C.N[C@H]1CCC[C@@H]1NC(=O)OC(C)(C)C>C(Cl)Cl.Cl.O1CCOCC1>[ClH:18].[NH2:24][C@H:23]1[CH2:25][CH2:26][CH2:27][C@@H:28]1[NH:20][C:7](=[O:9])[C:6]1[CH:10]=[C:2]([CH3:1])[CH:3]=[CH:4][C:5]=1[N:11]1[N:15]=[CH:14][CH:13]=[N:12]1

Participants

9

Reactant 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 181649HOAtHCID 17040218(1S,2S)-trans-N-Boc-1,2-cyclopentanediamineHCID 532601655-methyl-2-(2H-1,2,3-triazol-2-yl)benzoic acid2×

Product 1

HCID 118308085HCID 118308085, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 5-methyl-2-(2H-1,2,3-triazol-2-yl)benzoic acid (Intermediate 6; 254 mg, 1.25 mmol) in dry DCM (4.16 ml) was added EDC (359 mg, 1.87 mmol), 3H-[1,2,3]triazolo[4,5-b]pyridin-3-ol (255 mg, 1.87 mmol), triethylamine (6.9 ml, 4.99 mmol) and tert-butyl N-[(1S,2S)-2-aminocyclopentyl]carbamate (CAS number 586961-34-4; 250 mg, 1.25 mmol). The solution was stirred at room temperature under an atmosphere of nitrogen for 72 hours and then partitioned between DCM and water, filtered through a hydrophobic frit and concentrated in vacuo. This was then purified by column chromatography (silica, 0-100% ethyl acetate/petrol) to afford a pale white solid. This Boc protected intermediate was dissolved in HCl in 1,4-dioxane (4M, 3 ml) and stirred at room temperature for 17 hours. The reaction was concentrated in vacuo and azeotropically distilled with toluene to afford the title compound.

Workup

  1. custompartitioned between DCM and water
  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. customto afford a pale white solid
  6. stirringstirred at room temperature for 17 hours
  7. concentrationThe reaction was concentrated in vacuo
  8. distillationazeotropically distilled with toluene

Sources & evidence

ORD record
ord-3ea0c89a3c7d44e4b1cdf9e312a9537f
Source dataset
uspto-grants-2015_10
Patent number
US09156829B2

Reaction notes

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