Methanol → 2-(3-Cyano-6-(isoquinolin-3-ylamino)pyrazin-2-yloxy)acetic acid

HRID 40691Notes

Reaction equation

HRID 40691 reaction equation
[C:1]([C:3]1[C:4]([O:20][CH2:21][C:22]([O:24]CC)=[O:23])=[N:5][C:6]([NH:9][C:10]2[N:11]=[CH:12][C:13]3[C:18]([CH:19]=2)=[CH:17][CH:16]=[CH:15][CH:14]=3)=[CH:7][N:8]=1)#[N:2].[OH-].[Li+].CO>C1COCC1>[C:1]([C:3]1[C:4]([O:20][CH2:21][C:22]([OH:24])=[O:23])=[N:5][C:6]([NH:9][C:10]2[N:11]=[CH:12][C:13]3[C:18]([CH:19]=2)=[CH:17][CH:16]=[CH:15][CH:14]=3)=[CH:7][N:8]=1)#[N:2]

Participants

5

Reactant 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 44204747Ethyl 2-(3-cyano-6-(isoquinolin-3-ylamino)pyrazin-2-yloxy)acetate

Product 1

HCID 442047482-(3-Cyano-6-(isoquinolin-3-ylamino)pyrazin-2-yloxy)acetic acidYield 34%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 2-(3-cyano-6-(isoquinolin-3-ylamino)pyrazin-2-yloxy)acetate (35 mg, 0.099 mmol) was dissolved in THF (1 mL) and lithium hydroxide (2.4 mg, 0.099 mmol) added. The reaction was stirred at room temperature for 15 hours. Methanol (1 mL) was added and the reaction mixture was stirred for a further 24 hours and then concentrated to dryness. Purification by preparative HPLC afforded the title compound (10.8 mg, 0.0336 mmol, 34%). 1H NMR (MeOD, 400 MHz) δ 9.04 (s, 1H), 8.53 (s, 1H), 8.14-8.10 (m, 2H), 7.97 (d, 1H, J=8.0 Hz), 7.72-7.67 (m, 1H), 7.53-7.48 (m, 1H), 4.96 (br s, 2H), 2.67 (s, 1H). LC-MS (2) Rt=1.46 min; No ionization.

Workup

  1. stirringthe reaction mixture was stirred for a further 24 hours
  2. concentrationconcentrated to dryness
  3. customPurification by preparative HPLC

Sources & evidence

ORD record
ord-5523372a6bbe46c0bbce8e752a77b323
Source dataset
uspto-grants-2013_09
Patent number
US08530468B2

Reaction notes

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