Lithium Hydroxide → HCID 136198046, compound

HRID 1627226Notes

Reaction equation

HRID 1627226 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[C:7]([C:11]2[CH:12]=[C:13]3[C:17](=[CH:18][CH:19]=2)[N:16](C(O)=O)[C:15]([C:23]2[O:27][N:26]=[C:25]([CH3:28])[N:24]=2)=[CH:14]3)[N:8]([CH3:10])[N:9]=1)=[O:4].[Li+].[OH-]>O1CCCC1.CO.O>[CH3:10][N:8]1[C:7]([C:11]2[CH:12]=[C:13]3[C:17](=[CH:18][CH:19]=2)[NH:16][C:15]([C:23]2[O:27][N:26]=[C:25]([CH3:28])[N:24]=2)=[CH:14]3)=[CH:6][C:5]([C:3]([OH:4])=[O:2])=[N:9]1

Participants

6

Reactant 2

HCID 3939Lithium HydroxideHCID 66989786HCID 66989786, compound

Product 1

HCID 136198046HCID 136198046, compoundYield 83%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 5-(5-Methoxycarbonyl-2-methyl-2H-pyrazol-3-yl)-2-(3-methyl-1,2,4-oxadiazol-5-yl)-indole-1-carboxylic acid (2.7 g) in tetrahydrofuran (40 ml) and methanol (40 ml) at room temperature is added a solution of LiOH (3M, 103.3 mmol) in water over 5 minutes. The reaction is stirred for 30 minutes and the organic solvents are evaporated in vacuo. The reaction mixture is diluted 3x with water and washed with dichloromethane (100 ml). The aqueous layer is acidified with HCl (12 N) and the product extracted 3× with 200 ml of ethyl acetate. The combined ethyl acetate washings are dried (Na2SO4), filtered, and evaporated in vacuo to give the title compound 1.9 g, 57%, LC/MS ESI m/z (M+H)+=324.5.

Workup

  1. customthe organic solvents are evaporated in vacuo
  2. additionThe reaction mixture is diluted 3x with water
  3. washwashed with dichloromethane (100 ml)
  4. extractionthe product extracted 3× with 200 ml of ethyl acetate
  5. dry with materialThe combined ethyl acetate washings are dried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-d973053275cc481db87d25ec214e0958
Source dataset
uspto-grants-2014_07
Patent number
US08785489B2

Reaction notes

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