Methyl 4-chloroacetoacetate → Methyl (2'-{4-[2-(trifluoromethyl)phenoxy]piperidin-1-yl}-2,5'-bi-1,3-thiazol-4-yl)acetate

HRID 561203노트

반응식

HRID 561203 반응식
[F:1][C:2]([F:25])([F:24])[C:3]1[CH:23]=[CH:22][CH:21]=[CH:20][C:4]=1[O:5][CH:6]1[CH2:11][CH2:10][N:9]([C:12]2[S:13][C:14]([C:17](=[S:19])[NH2:18])=[CH:15][N:16]=2)[CH2:8][CH2:7]1.Cl[CH2:27][C:28](=O)[CH2:29][C:30]([O:32][CH3:33])=[O:31]>CO.O>[F:25][C:2]([F:1])([F:24])[C:3]1[CH:23]=[CH:22][CH:21]=[CH:20][C:4]=1[O:5][CH:6]1[CH2:11][CH2:10][N:9]([C:12]2[S:13][C:14]([C:17]3[S:19][CH:27]=[C:28]([CH2:29][C:30]([O:32][CH3:33])=[O:31])[N:18]=3)=[CH:15][N:16]=2)[CH2:8][CH2:7]1

참가 물질

5

반응물 2

HCID 36240Methyl 4-chloroacetoacetateHCID 866204572-{4-[2-(Trifluoromethyl)phenoxy]piperidin-1-yl}-1,3-thiazole-5-carbothioamide

생성물 1

HCID 86620458Methyl (2'-{4-[2-(trifluoromethyl)phenoxy]piperidin-1-yl}-2,5'-bi-1,3-thiazol-4-yl)acetate

시약·촉매·용매 2

HCID 887Methanol용매HCID 962Water용매

반응 조건

온도
82.5 °C

실험 절차

A mixture of 2-{4-[2-(trifluoromethyl)phenoxy]piperidin-1-yl}-1,3-thiazole-5-carbothioamide (240 mg, 0.62 mmol) and methyl 4-chloroacetoacetate (73 μL, 0.62 mmol) in methanol (3 mL) was heated in a sealed tube at 80-85° C. overnight. After cooling, the mixture was diluted with water and extracted with EtOAc. The EtOAc extract was washed twice with water, dried (Na2SO4) and concentrated. The crude material was purified by column chromatography on silica gel (eluting with 30-60% EtOAc/hexanes) to give the title compound as a pale yellow gum.

후처리

  1. temperatureAfter cooling
  2. extractionextracted with EtOAc
  3. extractionThe EtOAc extract
  4. washwas washed twice with water
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customThe crude material was purified by column chromatography on silica gel (eluting with 30-60% EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-84dadda0bd434f54a7d7e256accde99e
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08063224B2

반응 노트

불러오는 중…