3,3-Dimethylbutylamine → HCID 67273914, compound

HRID 598219Notes

Reaction equation

HRID 598219 reaction equation
Cl[C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][C:5]([F:13])=[CH:4][N:3]=1.[CH3:14][C:15]([CH3:20])([CH3:19])[CH2:16][CH2:17][NH2:18]>C(O)C.C(OCC)(=O)C>[CH3:14][C:15]([CH3:20])([CH3:19])[CH2:16][CH2:17][NH:18][C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][C:5]([F:13])=[CH:4][N:3]=1

Participants

5

Reactant 2

HCID 197093,3-DimethylbutylamineHCID 11390082Ethyl 2-chloro-5-fluoronicotinate

Product 1

HCID 67273914HCID 67273914, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
150 °C

Procedure

A solution of ethyl 2-chloro-5-fluoro-3-pyridinecarboxylate (0.300 g, 1.47 mmol) in ethanol (3.0 mL) was treated with (3,3-dimethylbutyl)amine (0.210 mL, 1.58 mmol). The mixture was heated to 150° C. for 0.5 h in a Biotage Initiator microwave synthesizer. The solution was diluted with ethyl acetate and washed with saturated aqueous sodium bicarbonate. The organic portion was dried over magnesium sulfate, filtered, and concentrated in vacuo. The title compound was obtained as an amber oil (0.347 g, 88%). 1H NMR (400 MHz, METHANOL-d4) δ ppm 6.61 (d, J=3.0 Hz, 1H), 6.30 (dd, J=8.8, 3.0 Hz, 1H), 6.24 (br. s., 1H), 2.80 (q, J=7.1 Hz, 2H), 1.88-1.99 (m, 2H), −0.02-0.09 (m, 2H), −0.14 (t, J=7.2 Hz, 3H), −0.53 (s, 9H). MS(ES+) m/e 269 [M+H]+.

Workup

  1. washwashed with saturated aqueous sodium bicarbonate
  2. dry with materialThe organic portion was dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e2285f50162e490c835a24f0733f3507
Source dataset
uspto-grants-2011_03
Patent number
US07897612B2

Reaction notes

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