Lithium hydroxide, monohydrate → 2-(3-Acetyl-5-(pyrimidin-2-ylmethoxy)-1H-indazol-1-yl)acetic acid

HRID 1527285Notes

Reaction equation

HRID 1527285 reaction equation
[C:1]([C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:13][CH2:14][C:15]3[N:20]=[CH:19][CH:18]=[CH:17][N:16]=3)[CH:11]=2)[N:6]([CH2:21][C:22]([O:24]C)=[O:23])[N:5]=1)(=[O:3])[CH3:2].O[Li].O>C1COCC1.O>[C:1]([C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:13][CH2:14][C:15]3[N:16]=[CH:17][CH:18]=[CH:19][N:20]=3)[CH:11]=2)[N:6]([CH2:21][C:22]([OH:24])=[O:23])[N:5]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 68283900Methyl 2-(3-acetyl-5-(pyrimidin-2-ylmethoxy)-1H-indazol-1-yl)acetate

Product 1

HCID 682840752-(3-Acetyl-5-(pyrimidin-2-ylmethoxy)-1H-indazol-1-yl)acetic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To methyl 2-(3-acetyl-5-(pyrimidin-2-ylmethoxy)-1H-indazol-1-yl)acetate (1.93 g, 5.67 mmol) in THF (15 mL) and water (15 mL) was added LiOH.H2O (0.25 g, 5.95 mmol). The reaction mixture was stirred at RT for 1.5 h. Volatiles were evaporated and the residue was freeze-dried overnight to give the title compound. MS (LC/MS): 327.0 [M+H]+, 325.1 [M+H]+; tR (HPLC conditions c): 3.24 min.

Workup

  1. customVolatiles were evaporated
  2. customthe residue was freeze-dried overnight

Sources & evidence

ORD record
ord-2864ecd1dab34fcf8e728e69de8dd071
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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