Water → HCID 57911772, compound

HRID 2389769Notes

Reaction equation

HRID 2389769 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][NH:5][C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9].Cl[C:14]1[N:19]=[C:18]([NH2:20])[C:17]([N+:21]([O-:23])=[O:22])=[CH:16][CH:15]=1.C(=O)(O)[O-].[K+].O>CN(C=O)C>[NH2:20][C:18]1[N:19]=[C:14]([NH:1][CH2:2][CH2:3][CH2:4][NH:5][C:6](=[O:12])[O:7][C:8]([CH3:9])([CH3:11])[CH3:10])[CH:15]=[CH:16][C:17]=1[N+:21]([O-:23])=[O:22]

Participants

6

Reactant 4

HCID 962WaterHCID 516893Potassium BicarbonateHCID 27240356-Chloro-3-nitropyridin-2-ylamineHCID 2735700tert-Butyl (3-aminopropyl)carbamate

Product 1

HCID 57911772HCID 57911772, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

150.6 mg (0.864 mmol) of tert-butyl (3-aminopropyl)carbamate, 300 mg (1.73 mmol) of 6-chloro-3-nitropyridine-2-amine and 173 mg (1.73 mmol) of potassium bicarbonate are suspended in 10 ml of DMF and heated at 90° C. for 16 h. Water is added to the mixture, which is then extracted three times with ethyl acetate. Purification of the crude product by preparative HPLC and drying under high vacuum result in 195 mg (65% of theory) of product.

Workup

  1. extractionis then extracted three times with ethyl acetate
  2. customPurification of the crude product by preparative HPLC
  3. customdrying under high vacuum
  4. customresult in 195 mg (65% of theory) of product

Sources & evidence

ORD record
ord-6d538a5295b541a48ddf96ad15065058
Source dataset
uspto-grants-2012_09
Patent number
US08273752B2

Reaction notes

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