Di(succinimido) carbonate → methyl 4-({[(2,5-dioxo-1-pyrrolidinyl)oxy]carbonyl}amino)-1H-indazole-1-carboxylate

HRID 586066Notes

Reaction equation

HRID 586066 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[N:5][N:6]2[C:11]([O:13][CH3:14])=[O:12].[O:15]=[C:16]1[CH2:20][CH2:19][C:18](=[O:21])[N:17]1[O:22][C:23](ON1C(=O)CCC1=O)=[O:24]>C(#N)C>[O:15]=[C:16]1[CH2:20][CH2:19][C:18](=[O:21])[N:17]1[O:22][C:23]([NH:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[N:5][N:6]2[C:11]([O:13][CH3:14])=[O:12])=[O:24]

Participants

4

Reactant 2

HCID 676246Di(succinimido) carbonateHCID 22032652methyl 4-amino-1H-indazole-1-carboxylate

Product 1

HCID 11313556methyl 4-({[(2,5-dioxo-1-pyrrolidinyl)oxy]carbonyl}amino)-1H-indazole-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Methyl 4-amino-1H-indazole-1-carboxylate (1.9 g, 10 mmol) and 1-({[(2,5-dioxo-1-pyrrolidinyl)oxy]carbonyl}oxy)-2,5-pyrrolidinedione (2.8 g, 11 mmol) were combined in acetonitrile (100 mL), stirred for 48 hours at ambient temperature, and filtered. The filter cake was washed with acetonitrile (10 mL) and dried under reduced pressure at ambient temperature to provide the title compound.

Workup

  1. filtrationfiltered
  2. washThe filter cake was washed with acetonitrile (10 mL)
  3. customdried under reduced pressure at ambient temperature

Sources & evidence

ORD record
ord-1036709ff8d24ddcb131c880f41056bd
Source dataset
uspto-grants-2005_08
Patent number
US06933311B2

Reaction notes

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