Methanol → 3-Amino-1-[(5-chloro-1-isobutyl-indazol-7-yl)methyl]indazole-5-carboxylic acid

HRID 2203184Notes

Reaction equation

HRID 2203184 reaction equation
[NH2:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]([O:13]C)=[O:12])[CH:9]=2)[N:4]([CH2:15][C:16]2[CH:17]=[C:18]([Cl:29])[CH:19]=[C:20]3[C:24]=2[N:23]([CH2:25][CH:26]([CH3:28])[CH3:27])[N:22]=[CH:21]3)[N:3]=1.[OH-].[Li+].O.CO>O1CCCC1>[NH2:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]([OH:13])=[O:12])[CH:9]=2)[N:4]([CH2:15][C:16]2[CH:17]=[C:18]([Cl:29])[CH:19]=[C:20]3[C:24]=2[N:23]([CH2:25][CH:26]([CH3:27])[CH3:28])[N:22]=[CH:21]3)[N:3]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 3939Lithium HydroxideHCID 118251621Methyl 3-amino-1-[(5-chloro-1-isobutyl-indazol-7-yl)methyl]indazole-5-carboxylate

Product 1

HCID 1182516143-Amino-1-[(5-chloro-1-isobutyl-indazol-7-yl)methyl]indazole-5-carboxylic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of compound 67 (0.045 g, 0.11 mmol), lithium hydroxide (0.02 g, 0.44 mmol) in a mixture of tetrahydrofuran (2 mL), water (1 mL) and methanol (1 mL) was heated at 100° C. under microwave conditions for 10 minutes. Then, the reaction was quenched by adding water and diluted with ethyl acetate. The organic layer was separated, washed with Brine, dried (MgSO4), filtered and the solvent was evaporated.

Workup

  1. customThen, the reaction was quenched
  2. additionby adding water
  3. additiondiluted with ethyl acetate
  4. customThe organic layer was separated
  5. washwashed with Brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customthe solvent was evaporated

Sources & evidence

ORD record
ord-0c95e56709dd445f9add29046f8b502b
Source dataset
uspto-grants-2016_06
Patent number
US09365569B2

Reaction notes

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