Morpholine → 2-Ethylsulfanyl-4-methyl-6-morpholin-4-yl-pyridine-3-carboxylic acid

HRID 1039735노트

반응식

HRID 1039735 반응식
Cl[C:2]1[N:7]=[C:6]([S:8][CH2:9][CH3:10])[C:5]([C:11]([OH:13])=[O:12])=[C:4]([CH3:14])[CH:3]=1.[NH:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1>[OH-].[Na+]>[CH2:9]([S:8][C:6]1[C:5]([C:11]([OH:13])=[O:12])=[C:4]([CH3:14])[CH:3]=[C:2]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[N:7]=1)[CH3:10]

참가 물질

4

반응물 2

HCID 8083MorpholineHCID 866643126-Chloro-2-ethylsulfanyl-4-methyl-pyridine-3-carboxylic acid

생성물 1

HCID 672874632-Ethylsulfanyl-4-methyl-6-morpholin-4-yl-pyridine-3-carboxylic acid수율 49%

시약·촉매·용매 1

HCID 14798Sodium Hydroxide용매

반응 조건

온도
105 °C

실험 절차

A mixture of 12.0 g (51.7 mmol) 6-chloro-2-ethylsulfanyl-4-methyl-pyridine-3-carboxylic acid and 33.7 g (387 mmol) morpholine was heated to 105° C. for 5 d. After cooling to RT a 2M aq. NaOH sol. (200 ml) was added, followed by washing with ether (3×200 ml). The aqueous layer was then acidified with a 2M aq. HCl to pH 5 and extracted with EtOAc. In the same manner pH 4 was adjusted followed by extraction with EtOAc. The combined EtOAc extracts were dried over MgSO4 and concentrated in vacuo. Crystallisation (DCM/hexane) of the residue yielded 7.2 g (25.3 mmol, 49%) 2-ethylsulfanyl-4-methyl-6-morpholin-4-yl-pyridine-3-carboxylic acid.

후처리

  1. additionwas added
  2. washby washing with ether (3×200 ml)
  3. extractionextracted with EtOAc
  4. extractionIn the same manner pH 4 was adjusted followed by extraction with EtOAc
  5. dry with materialThe combined EtOAc extracts were dried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customCrystallisation (DCM/hexane) of the residue

출처 및 근거

ORD 기록
ord-1d2b465358b14875b106833e3124d23a
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08552200B2

반응 노트

불러오는 중…