Triethylamine → Methyl 5-chloro-2-(3-hydroxyazetidin-1-yl)nicotinate

HRID 72429

반응식

HRID 72429 반응식
Cl.[OH:2][CH:3]1[CH2:6][NH:5][CH2:4]1.C(N(CC)CC)C.Cl[C:15]1[N:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:16]=1[C:17]([O:19][CH3:20])=[O:18]>O1CCCC1.CO>[Cl:25][C:22]1[CH:23]=[N:24][C:15]([N:5]2[CH2:6][CH:3]([OH:2])[CH2:4]2)=[C:16]([CH:21]=1)[C:17]([O:19][CH3:20])=[O:18]

참가 물질

5

반응물 3

HCID 8471Triethylamine2회HCID 27592903-Hydroxyazetidine hydrochloride2회HCID 2764318Methyl 2,5-Dichloronicotinate

생성물 1

HCID 67958303Methyl 5-chloro-2-(3-hydroxyazetidin-1-yl)nicotinate수율 76.6%

시약·촉매·용매 1

HCID 21899815MeOH tetrahydrofuran용매

반응 조건

온도
75 °C

실험 절차

To a mixture of 3-Hydroxyazetidine hydrochloride (37.17 g, 0.339 mol) and triethylamine (70.93 ml, 0.508 mol) in tetrahydrofuran/methanol (840/280 ml) Methyl 2,5-dichloronicotinate (70 g, 0.339 mol) was added and the resulting mixture was heated at 75° C. for 4 hours then at 62° C. overnight. 3-Hydroxyazetidine hydrochloride (3.7 g, 0.03 mol) and triethylamine (23.60 ml, 0.16 mol) were added and the reaction mixture was further heated at 80° C. for 28 h. Solvents were evaporated in vacuo. The residue was taken in dichloromethane (400 ml) and water (500 ml). The formed solid was filtered, washed with water (500 ml) and dried in vacuum to afford a first batch of the title compound (D62) (63 g).

후처리

  1. additionwas added
  2. customat 62° C.
  3. customovernight
  4. temperaturethe reaction mixture was further heated at 80° C. for 28 h
  5. customSolvents were evaporated in vacuo
  6. filtrationThe formed solid was filtered
  7. washwashed with water (500 ml)
  8. customdried in vacuum

출처 및 근거

ORD 기록
ord-25e4a4f6a52f415abe7623234769fe0c
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08828987B2

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