Di(succinimido) carbonate → tert-butyl {2-[4-({[(2,5-dioxopyrrolidin-1-yl)oxy]carbonyl}amino)-2-(1-methyl-1H-pyrazol-5-yl)phenoxy]ethyl}carbamate

HRID 521622Notes

Reaction equation

HRID 521622 reaction equation
C1C(=O)N(O[C:9]([O:11][N:12]2[C:17](=[O:18])[CH2:16][CH2:15][C:13]2=[O:14])=[O:10])C(=O)C1.[NH2:19][C:20]1[CH:36]=[CH:35][C:23]([O:24][CH2:25][CH2:26][NH:27][C:28](=[O:34])[O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[C:22]([C:37]2[N:41]([CH3:42])[N:40]=[CH:39][CH:38]=2)[CH:21]=1>CN(C)C=O>[O:18]=[C:17]1[CH2:16][CH2:15][C:13](=[O:14])[N:12]1[O:11][C:9]([NH:19][C:20]1[CH:36]=[CH:35][C:23]([O:24][CH2:25][CH2:26][NH:27][C:28](=[O:34])[O:29][C:30]([CH3:33])([CH3:31])[CH3:32])=[C:22]([C:37]2[N:41]([CH3:42])[N:40]=[CH:39][CH:38]=2)[CH:21]=1)=[O:10]

Participants

4

Reactant 2

HCID 676246Di(succinimido) carbonateHCID 67265127tert-butyl 2-(4-amino-2-(1-methyl-1H-pyrazol-5-yl)phenoxy)ethylcarbamate

Product 1

HCID 86633178tert-butyl {2-[4-({[(2,5-dioxopyrrolidin-1-yl)oxy]carbonyl}amino)-2-(1-methyl-1H-pyrazol-5-yl)phenoxy]ethyl}carbamate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

N,N′-Disuccinimidyl carbonate (262 mg, 1.2 eq) was dissolved in 6 mL dimethylformamide and cooled to 0° C. To this was added the tert-butyl 2-(4-amino-2-(1-methyl-1H-pyrazol-5-yl)phenoxy)ethylcarbamate (242 mg, 0.95 mmol) dissolved in 4 mL dimethylformamide, drop-wise over 30 mins. The solution was removed from the ice bath and stirred at room temperature for 2 hr, then moved to an oil bath and stirred at 65° C. for 30 minutes. The mixture was used without further purification.

Workup

  1. customThe solution was removed from the ice bath
  2. custommoved to an oil bath
  3. stirringstirred at 65° C. for 30 minutes
  4. customThe mixture was used without further purification

Sources & evidence

ORD record
ord-2b95399297c5446497148df7ef912e6b
Source dataset
uspto-grants-2016_05
Patent number
US09328107B2

Reaction notes

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