Hydrochloric Acid → HCID 178457015, compound

HRID 1946814Notes

Reaction equation

HRID 1946814 reaction equation
[CH:1]1([CH2:4][N:5]([CH2:30][CH2:31][CH3:32])[C:6]2[N:11]=[CH:10][N:9]=[C:8]([C:12]([NH:14][C:15]3[CH:16]=[C:17]4[C:21](=[CH:22][CH:23]=3)[NH:20][N:19]=[C:18]4[CH2:24][CH2:25][C:26]([O:28]C)=[O:27])=[O:13])[CH:7]=2)[CH2:3][CH2:2]1.[OH-].[Na+].Cl>C(O)C>[CH:1]1([CH2:4][N:5]([CH2:30][CH2:31][CH3:32])[C:6]2[N:11]=[CH:10][N:9]=[C:8]([C:12]([NH:14][C:15]3[CH:16]=[C:17]4[C:21](=[CH:22][CH:23]=3)[NH:20][N:19]=[C:18]4[CH2:24][CH2:25][C:26]([OH:28])=[O:27])=[O:13])[CH:7]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 178457016HCID 178457016, compound

Product 1

HCID 178457015HCID 178457015, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of methyl 3-{5-[({6-[(cyclopropylmethyl)(propyl)amino]pyrimidin-4-yl}carbonyl)amino]-1H-indazol-3-yl}propanoate (Example 123, 20 mg; 0.05 mmol) in ethanol (1 ml) was treated with 10% sodium hydroxide solution (1 ml). After stirring at RT for 2 hours the mixture was acidified to pH 3 with dilute HCl and extracted with EtOAc. The combined organic extracts were passed through a hydrophobic frit and the solvent removed in vacuo. The residue was purified by column chromatography (silica) eluting with EtOAc containing increasing amounts MeOH of to give the title compound as a white solid.

Workup

  1. extractionextracted with EtOAc
  2. customthe solvent removed in vacuo
  3. customThe residue was purified by column chromatography (silica)
  4. washeluting with EtOAc containing
  5. temperatureincreasing amounts MeOH of

Sources & evidence

ORD record
ord-dcf6b9cfd00d40d39a0f62290f60df9f
Source dataset
uspto-grants-2013_03
Patent number
US08399448B2

Reaction notes

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