Ethyl chloroformate → HCID 57593549, compound

HRID 1785302Notes

Reaction equation

HRID 1785302 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][NH:5][C:6]1[C:11]([Br:12])=[CH:10][N:9]=[C:8]([NH:13][C:14]2[CH:15]=[C:16]([NH:20][C:21]([N:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)=[O:22])[CH:17]=[CH:18][CH:19]=2)[N:7]=1.Cl[C:29]([O:31][CH2:32][CH3:33])=[O:30]>N1C=CC=CC=1>[CH2:32]([O:31][C:29](=[O:30])[NH:1][CH2:2][CH2:3][CH2:4][NH:5][C:6]1[C:11]([Br:12])=[CH:10][N:9]=[C:8]([NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([NH:20][C:21]([N:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)=[O:22])[CH:15]=2)[N:7]=1)[CH3:33]

Participants

4

Reactant 2

HCID 10928Ethyl chloroformateHCID 57593297HCID 57593297, compound

Product 1

HCID 57593549HCID 57593549, compoundYield 6.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of N-(3-((4-((3-aminopropyl)amino)-5-bromo-2-pyrimidinyl)amino)phenyl)-1-pyrrolidinecarboxamide (150 mg, 0.30 mmol) in pyridine (5 mL) was added ethyl chloroformate (38.5 mg, 0.35 mmol) at 0° C. under N2. The resulting reaction mixture was stirred at 0° C. for 1 h and then was stirred at room temperature overnight. The mixture was washed with water (3×50 mL). Then the reaction mixture was concentrated. Purification by HPLC chromatography using acetonitrile/water gave the title compound (10 mg).

Workup

  1. customThe resulting reaction mixture
  2. stirringwas stirred at room temperature overnight
  3. washThe mixture was washed with water (3×50 mL)
  4. concentrationThen the reaction mixture was concentrated
  5. customPurification by HPLC chromatography

Sources & evidence

ORD record
ord-b16ead9bbb0d438d90be65935a9f0c13
Source dataset
uspto-grants-2009_03
Patent number
US07504410B2

Reaction notes

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