Potassium Carbonate → [3-(6-Methoxy-3-nitro-pyridin-2-ylamino)-propyl]-carbamic acid tert-butyl ester

HRID 1801458Notes

Reaction equation

HRID 1801458 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([O:11][CH3:12])[N:3]=1.[C:13]([O:17][C:18]([NH:20][CH2:21][CH2:22][CH2:23][NH2:24])=[O:19])([CH3:16])([CH3:15])[CH3:14].C([O-])([O-])=O.[K+].[K+]>CC#N.CN(C=O)C>[C:13]([O:17][C:18](=[O:19])[NH:20][CH2:21][CH2:22][CH2:23][NH:24][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([O:11][CH3:12])[N:3]=1)([CH3:16])([CH3:14])[CH3:15]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 2735700tert-Butyl (3-aminopropyl)carbamateHCID 27950292-Chloro-6-methoxy-3-nitropyridine

Product 1

HCID 68631911[3-(6-Methoxy-3-nitro-pyridin-2-ylamino)-propyl]-carbamic acid tert-butyl esterYield 96.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of 2-chloro-6-methoxy-3-nitropyridine (5.9 g; commercial), N-(tert-butoxycarbonyl)-1,3-propanediamine (4.48 g; commercial) and K2CO3 (3.55 g) in MeCN (90 mL) and DMF (25 mL) was heated at 40° C. for 30 min. The reaction mixture was filtered and the filtrate was evaporated under reduced pressure. The residue was taken up in EA, sequentially washed with water and brine and evaporated under reduced pressure, affording 8.1 g (96% yield) of a crude yellow solid which was used in the next step without further purification.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe filtrate was evaporated under reduced pressure
  3. washsequentially washed with water and brine
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-556912d0069e4d7fb161e5c767c13ca7
Source dataset
uspto-grants-2013_01
Patent number
US08349826B2

Reaction notes

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