Lithium Hydroxide → HCID 58137788, compound

HRID 2189448Notes

Reaction equation

HRID 2189448 reaction equation
[Cl:1][C:2]1[CH:31]=[CH:30][C:5]2[N:6]=[C:7]([NH:9][C:10]3[CH:15]=[CH:14][C:13]([C:16]4[N:20]5[CH:21]=[CH:22][CH:23]=[C:24]([C:25]([O:27]CC)=[O:26])[C:19]5=[N:18][N:17]=4)=[CH:12][CH:11]=3)[S:8][C:4]=2[CH:3]=1.[Li+].[OH-]>C1COCC1>[Cl:1][C:2]1[CH:31]=[CH:30][C:5]2[N:6]=[C:7]([NH:9][C:10]3[CH:11]=[CH:12][C:13]([C:16]4[N:20]5[CH:21]=[CH:22][CH:23]=[C:24]([C:25]([OH:27])=[O:26])[C:19]5=[N:18][N:17]=4)=[CH:14][CH:15]=3)[S:8][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 58137792HCID 58137792, compound

Product 1

HCID 58137788HCID 58137788, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of ethyl 3-(4-(6-chlorobenzo[d]thiazol-2-ylamino)phenyl)-[1,2,4]triazolo[4,3-a]pyridine-8-carboxylate (935 mg, 2.08 mmol) in THF (20 mL) was added 1 N aqueous LiOH solution (4 mL, 4 mmol). The mixture was stirred at room temperature overnight, concentrated to one third of the initial volume, and then acidified with 1 N aqueous HCl. To the resulting precipitate was added water (15 mL) and CH2Cl2 (5 mL). After stirring for 15 min, the precipitate was isolated by filtration, rinsed with water and CH2Cl2, and then air dried to yield the title compound as a brown solid (790 mg, 90%). HPLC/MS (Method C): retention time=1.92 min, [M+H]+=422.3.

Workup

  1. concentrationconcentrated to one third of the initial volume
  2. additionTo the resulting precipitate was added water (15 mL) and CH2Cl2 (5 mL)
  3. stirringAfter stirring for 15 min
  4. customthe precipitate was isolated by filtration
  5. washrinsed with water and CH2Cl2
  6. customair dried

Sources & evidence

ORD record
ord-570ba510594a45f7ab1a4a9c70b16ef3
Source dataset
uspto-grants-2012_12
Patent number
US08324241B2

Reaction notes

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