Acetic Acid → HCID 70498679, compound

HRID 1045488Notes

Reaction equation

HRID 1045488 reaction equation
C(O[C:6](=[O:17])[NH:7][C:8]1[C:13]([CH:14]=[O:15])=[C:12]([Cl:16])[CH:11]=[CH:10][N:9]=1)(C)(C)C.[NH2:18][CH2:19][CH2:20]O.CC(O)=O>C1(C)C=CC=CC=1>[Cl:16][C:12]1[C:13]2[CH:14]3[O:15][CH2:20][CH2:19][N:18]3[C:6](=[O:17])[NH:7][C:8]=2[N:9]=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 700EthanolamineHCID 46204204tert-Butyl 4-chloro-3-formylpyridin-2-ylcarbamate

Product 1

HCID 70498679HCID 70498679, compoundYield 15.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

tert-Butyl(4-chloro-3-formylpyridin-2-yl)carbamate (2.0 g, 7.79 mmol), 2-aminoethanol (0.57 g, 9.35 mmol), and AcOH (0.47 g; 7.79 mmol) were suspended in toluene (20 mL), and stirred overnight at room temperature. The reaction mixture was concentrated, and suspended in hexanes/ether (5/1, v/v). The resulting precipitate was filtered, suspended in NMP (3 mL) in 20 ml seal tube, and heated for 30 min. at 150° C. The crude product was purified directly via HPLC to provide 42 (270 mg, 10% yield) as a solid. LC-MS (M+H=226, obsd.=226).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. filtrationThe resulting precipitate was filtered
  3. customseal tube
  4. temperatureheated for 30 min. at 150° C
  5. customThe crude product was purified directly via HPLC

Sources & evidence

ORD record
ord-d9b9bceda64a4607917b6270c90f2013
Source dataset
uspto-grants-2013_10
Patent number
US08569295B2

Reaction notes

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