Hydrochloric Acid → 5-[(3S)-3-pyrrolidinylmethyl]-4-[4-(7-quinolinyl)phenyl]-2,4-dihydro-3H-1,2,4-triazol-3-one Hydrochloride

HRID 525258Notes

Reaction equation

HRID 525258 reaction equation
[O:1]=[C:2]1[NH:6][N:5]=[C:4]([CH2:7][C@@H:8]2[CH2:12][CH2:11][N:10](C(OC(C)(C)C)=O)[CH2:9]2)[N:3]1[C:20]1[CH:25]=[CH:24][C:23]([C:26]2[CH:35]=[C:34]3[C:29]([CH:30]=[CH:31][CH:32]=[N:33]3)=[CH:28][CH:27]=2)=[CH:22][CH:21]=1.[ClH:36]>O1CCOCC1>[ClH:36].[NH:10]1[CH2:11][CH2:12][C@@H:8]([CH2:7][C:4]2[N:3]([C:20]3[CH:21]=[CH:22][C:23]([C:26]4[CH:35]=[C:34]5[C:29]([CH:30]=[CH:31][CH:32]=[N:33]5)=[CH:28][CH:27]=4)=[CH:24][CH:25]=3)[C:2](=[O:1])[NH:6][N:5]=2)[CH2:9]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 673769061,1-dimethylethyl (3S)-3-({5-oxo-4-[4-(7-quinolinyl)phenyl]-4,5-dihydro-1H-1,2,4-triazol-3-yl}methyl)-1-pyrrolidinecarboxylate

Product 1

HCID 673764885-[(3S)-3-pyrrolidinylmethyl]-4-[4-(7-quinolinyl)phenyl]-2,4-dihydro-3H-1,2,4-triazol-3-one HydrochlorideYield 96%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Into an 8 mL vial was placed 1,1-dimethylethyl (3S)-3-({5-oxo-4-[4-(7-quinolinyl)phenyl]-4,5-dihydro-1H-1,2,4-triazol-3-yl}methyl)-1-pyrrolidinecarboxylate (0.382 mmol). Added was 4N HCl in dioxane (2.0 mL). The vial was capped and the solution was agitated at room temperature for 1 h. The reaction was concentrated in vacuo to afford the title compound as the HCl salt (150 mg, 96%). No further purification was performed on this compound. MS(ES)+ m/e 372.2 [M+H]+.

Workup

  1. additionAdded
  2. customThe vial was capped
  3. concentrationThe reaction was concentrated in vacuo

Sources & evidence

ORD record
ord-c856d35a70ae4f008fa46d121a90e56a
Source dataset
uspto-grants-2016_05
Patent number
US09340529B2

Reaction notes

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