Acetic Acid → HCID 86732458, compound

HRID 1776432Notes

Reaction equation

HRID 1776432 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[CH2:12][N:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]([C:22]2[N:27]=[C:26]([NH:28][C:29]3[CH:34]=[CH:33][N:32]=[CH:31][CH:30]=3)[C:25]([O:35][CH3:36])=[CH:24][N:23]=2)=[N:14]1)[C:5]([O:7]C)=[O:6].[OH-].[Na+].C(O)(=O)C>CO.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[CH2:12][N:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]([C:22]2[N:27]=[C:26]([NH:28][C:29]3[CH:34]=[CH:33][N:32]=[CH:31][CH:30]=3)[C:25]([O:35][CH3:36])=[CH:24][N:23]=2)=[N:14]1)[C:5]([OH:7])=[O:6]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 71553360HCID 71553360, compound

Product 1

HCID 86732458HCID 86732458, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

150 mg of methyl 3-chloro-4-({3-[5-methoxy-4-(pyridin-4-ylamino)pyrimidin-2-yl]-1H-indazol-1-yl}methyl)benzoate (2-11-1, 0.299 mmol, 1. eq.) were dissolved in 0.364 ml of methanol. 60 mg of sodium hydroxid (1.50 mmol, 5 eq.) were added. The reaction mixture was stirred at room temperature for 3 hours. The resulting suspension was neutralised with acetic acid. The solution was diluted with ethyl acetate. The occurred precipitate was filtered off and washed with ethyl acetate and was dried in vacuo at 50° C. to yield 138 mg (0.28 mmol, 92.8%) of the analytically pure target compound.

Workup

  1. filtrationThe occurred precipitate was filtered off
  2. washwashed with ethyl acetate
  3. customwas dried in vacuo at 50° C.
  4. customto yield 138 mg (0.28 mmol, 92.8%) of the analytically pure target compound

Sources & evidence

ORD record
ord-7a0238f5d6a24b2e825d8edf0cb86176
Source dataset
uspto-grants-2016_02
Patent number
US09265763B2

Reaction notes

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