methyl 2-(4-(tert-butoxycarbonylamino)-1H-indazol-1-yl)-2-(4-chlorophenyl)butanoate → methyl 2-(4-amino-1H-indazol-1-yl)-2-(4-chlorophenyl)butanoate

HRID 1427230Notes

Reaction equation

HRID 1427230 reaction equation
C(OC([NH:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[CH:11]=[N:12][N:13]2[C:18]([C:25]1[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=1)([CH2:23][CH3:24])[C:19]([O:21][CH3:22])=[O:20])=O)(C)(C)C>Cl.CO>[NH2:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[CH:11]=[N:12][N:13]2[C:18]([C:25]1[CH:26]=[CH:27][C:28]([Cl:31])=[CH:29][CH:30]=1)([CH2:23][CH3:24])[C:19]([O:21][CH3:22])=[O:20]

Participants

3

Reactant 1

HCID 70562967methyl 2-(4-(tert-butoxycarbonylamino)-1H-indazol-1-yl)-2-(4-chlorophenyl)butanoate

Product 1

HCID 70561351methyl 2-(4-amino-1H-indazol-1-yl)-2-(4-chlorophenyl)butanoate

Reagents, catalysts & solvents 1

HCID 21893726Hydrochloride methanolSolvent

Procedure

A mixture of methyl 2-(4-(tert-butoxycarbonylamino)-1H-indazol-1-yl)-2-(4-chlorophenyl)butanoate (3.0 g, 6.8 mmol), as described in Example 18 Step D, in 4 N HCl/MeOH (20 mL) was stirred at room temperature for 2 h. After removing the solvent, the residue was dissolved in ethyl acetate (80 mL), pH value adjusted to 9-10 with saturated sodium bicarbonate solution, dried over sodium sulfate, then filtered. After removing the organic solvent, the residue was used for the next step without purification. LC/MS m/z=344.1 [M+H]+.

Workup

  1. customAfter removing the solvent
  2. dissolutionthe residue was dissolved in ethyl acetate (80 mL)
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customAfter removing the organic solvent
  6. customthe residue was used for the next step without purification

Sources & evidence

ORD record
ord-e065240689d4441986da8b415d686027
Source dataset
uspto-grants-2015_01
Patent number
US08933113B2

Reaction notes

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