Lithium Hydroxide → HCID 178461882, compound

HRID 1396626Notes

Reaction equation

HRID 1396626 reaction equation
[N:1]1[C:9]([NH:10][C@H:11]([C:13]2[N:14]=[C:15]([O:24][CH2:25][C:26]([O:28]C)=[O:27])[C:16]3[C:21]([CH:22]=2)=[CH:20][CH:19]=[CH:18][C:17]=3[Cl:23])[CH3:12])=[C:8]2[C:4]([NH:5][CH:6]=[N:7]2)=[N:3][CH:2]=1.[Li+].[OH-]>CCO.O>[N:1]1[C:9]([NH:10][C@H:11]([C:13]2[N:14]=[C:15]([O:24][CH2:25][C:26]([OH:28])=[O:27])[C:16]3[C:21]([CH:22]=2)=[CH:20][CH:19]=[CH:18][C:17]=3[Cl:23])[CH3:12])=[C:8]2[C:4]([NH:5][CH:6]=[N:7]2)=[N:3][CH:2]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 178501791HCID 178501791, compound

Product 1

HCID 178461882HCID 178461882, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To a mixture of (S)-methyl 2-(3-(1-(9H-purin-6-ylamino)ethyl)-8-chloroisoquinolin-1-yloxy)acetate 127 (200 mg, 0.47 mmol, 1.0 eq) in EtOH (5 mL) and H2O (2 mL), LiOH (78 mg, 3.25 mmol, 6.9 eq) was added in one portion. The resulting mixture was stirred at 60° C. for 2 h and then concentrated in vacuo. The residue was suspended in ice-water (15 mL) and the resulting mixture was neutralized with acetic acid at 0-5° C. to adjust pH to 7-8. The precipitate was collected by filtration and dried in vacuo to afford the product (S)-2-(3-(1-(9H-purin-6-ylamino)ethyl)-8-chloroisoquinolin-1-yloxy)acetic acid 128. ESI-MS m/z: 399.0 [M+H]+.

Workup

  1. additionwas added in one portion
  2. concentrationconcentrated in vacuo
  3. customwas neutralized with acetic acid at 0-5° C.
  4. filtrationThe precipitate was collected by filtration
  5. customdried in vacuo

Sources & evidence

ORD record
ord-4fd487ec596449779fb4158dabe765c8
Source dataset
uspto-grants-2014_12
Patent number
US08901133B2

Reaction notes

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