Tert-butyl-3-amino-5-{3-[2-(3-methoxyphenyl)ethyl]ureido}indazole-1-carboxylate → 1-(3-amino-1H-indazol-5-yl)-3-[2-(3-methoxyphenyl)ethyl]-urea

HRID 222387Notes

Reaction equation

HRID 222387 reaction equation
C(OC([N:8]1[C:16]2[C:11](=[CH:12][C:13]([NH:17][C:18]([NH:20][CH2:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([O:29][CH3:30])[CH:24]=3)=[O:19])=[CH:14][CH:15]=2)[C:10]([NH2:31])=[N:9]1)=O)(C)(C)C>Cl.O1CCOCC1>[NH2:31][C:10]1[C:11]2[C:16](=[CH:15][CH:14]=[C:13]([NH:17][C:18]([NH:20][CH2:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([O:29][CH3:30])[CH:24]=3)=[O:19])[CH:12]=2)[NH:8][N:9]=1

Participants

3

Reactant 1

HCID 68918447Tert-butyl-3-amino-5-{3-[2-(3-methoxyphenyl)ethyl]ureido}indazole-1-carboxylate

Product 1

HCID 250102231-(3-amino-1H-indazol-5-yl)-3-[2-(3-methoxyphenyl)ethyl]-urea

Reagents, catalysts & solvents 1

HCID 204431481,4-Dioxane hydrochlorideSolvent

Procedure

6.2 700 mg of tert-butyl-3-amino-5-{3-[2-(3-methoxyphenyl)ethyl]-ureido}indazole-1-carboxylate (1.6 mmol) are stirred for 16 hours with 10 ml of HCl/dioxane (4 M). The batch is concentrated and evaporated three times with 10 ml of toluene each time in a rotary evaporator. The residue is purified by column chromatography on silica gel (eluent: dichloromethane:methanol 9:1). Drying gives 120 mg of “A20” (22%), MS-FAB (M+H+)=326,

Workup

  1. concentrationThe batch is concentrated
  2. customevaporated three times with 10 ml of toluene each time
  3. customin a rotary evaporator
  4. customThe residue is purified by column chromatography on silica gel (eluent: dichloromethane:methanol 9:1)
  5. customDrying
  6. customgives 120 mg of “A20” (22%), MS-FAB (M+H+)=326

Sources & evidence

ORD record
ord-af9a103229f2478aad2d769d8b3d2c26
Source dataset
uspto-grants-2012_06
Patent number
US08207210B2

Reaction notes

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