Benzyl 2-(2-amino-5-bromopyridin-3-ylamino)-2-oxoethyl(methyl)carbamate → HCID 66820271, compound

HRID 241026Notes

Reaction equation

HRID 241026 reaction equation
[C:1]1([CH2:7][O:8][C:9](=[O:24])[N:10]([CH2:12][C:13]([NH:15][C:16]2[C:17]([NH2:23])=[N:18][CH:19]=[C:20]([Br:22])[CH:21]=2)=O)[CH3:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>C(O)(=O)C>[C:1]1([CH2:7][O:8][C:9](=[O:24])[N:10]([CH2:12][C:13]2[NH:15][C:16]3[C:17]([N:23]=2)=[N:18][CH:19]=[C:20]([Br:22])[CH:21]=3)[CH3:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 1

HCID 66819997Benzyl 2-(2-amino-5-bromopyridin-3-ylamino)-2-oxoethyl(methyl)carbamate

Product 1

HCID 66820271HCID 66820271, compoundYield 77.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of phenylmethyl{2-[(2-amino-5-bromopyridin-3-yl)amino]-2-oxoethyl}methylcarbamate (0.30 g, 0.76 mmol) in acetic acid (7.5 mL) was heated in a microwave apparatus (250 W) for 30 min. at 120° C. After cooling it to room temperature the reaction mixture was concentrated and the pH was adjusted to 8 by the addition of saturated aqueous sodium bicarbonate. The precipitating solid was collected by filtration, washed with water and dried in vacuo to give phenylmethyl[(6-bromo-1H-imidazo[4,5-b]pyridin-2-yl)methyl]methylcarbamate (0.22 g, 76%). MS (EI) for C16H15BrN4O2: 376 (MH+).

Workup

  1. concentrationwas concentrated
  2. additionthe pH was adjusted to 8 by the addition of saturated aqueous sodium bicarbonate
  3. filtrationThe precipitating solid was collected by filtration
  4. washwashed with water
  5. customdried in vacuo

Sources & evidence

ORD record
ord-2aac2f44d8d54b8db494c53ea2bc18e2
Source dataset
uspto-grants-2014_02
Patent number
US08648066B2

Reaction notes

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