Hydrochloric Acid → 5-[5-(4-Chloro-phenyl)-2-oxo-6H-[1,3,4]oxadiazin-3-ylmethyl]-3-methyl-sulphanyl-1,3-dihydro-indol-2-one

HRID 44291

반응식

HRID 44291 반응식
C(OC(=O)C[S:6]C)C.[NH2:9][C:10]1[CH:30]=[CH:29][C:13]([CH2:14][N:15]2[N:20]=[C:19]([C:21]3[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=3)[CH2:18][O:17][C:16]2=[O:28])=[CH:12][CH:11]=1.[C:31]([O:35]Cl)(C)(C)C.C(N([CH2:42][CH3:43])CC)C.Cl>C1COCC1>[Cl:27][C:24]1[CH:25]=[CH:26][C:21]([C:19]2[CH2:18][O:17][C:16](=[O:28])[N:15]([CH2:14][C:13]3[CH:29]=[C:30]4[C:10](=[CH:11][CH:12]=3)[N:9]([SH:6])[C:31](=[O:35])[CH:42]4[CH3:43])[N:20]=2)=[CH:22][CH:23]=1

참가 물질

7

반응물 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 78199Ethyl (methylthio)acetateHCID 521297Tert-Butyl hypochloriteHCID 666364683-(4-Amino-benzyl)-5-(4-chloro-phenyl)-3,6-dihydro-[1,3,4]oxadiazin-2-one

생성물 1

HCID 866624325-[5-(4-Chloro-phenyl)-2-oxo-6H-[1,3,4]oxadiazin-3-ylmethyl]-3-methyl-sulphanyl-1,3-dihydro-indol-2-one

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-60 °C

실험 절차

Ethyl(methylsulphanyl)acetate (27.31 mmoles) is added dropwise to a solution of the compound obtained in Step E (23.75 mmoles) in THF (200 ml) at −60° C. under a nitrogen atmosphere. tBuOCl (27.31 mmoles) is added dropwise to the reaction mixture over 20 minutes, keeping the temperature between −60° C. and −55° C. After stirring for 3 hours at −60° C., triethylamine (29.68 mmoles) is added dropwise. The reaction mixture is brought to ambient temperature; aqueous 3M HCl solution (340 ml) is then added and stirring is carried out for a further 2 hours. The organic phase is evaporated and the aqueous suspension is extracted with DCM. The organic phases are combined, then washed with 2M HCl solution and then with saturated NaCl solution, dried over sodium sulphate, filtered and evaporated to dryness. The residue is triturated in ethyl ether, filtered and dried in vacuo to yield the title product, which is used directly in the next Step.

후처리

  1. customthe temperature between −60° C. and −55° C
  2. customis brought to ambient temperature
  3. stirringstirring
  4. waitis carried out for a further 2 hours
  5. customThe organic phase is evaporated
  6. extractionthe aqueous suspension is extracted with DCM
  7. washwashed with 2M HCl solution
  8. dry with materialwith saturated NaCl solution, dried over sodium sulphate
  9. filtrationfiltered
  10. customevaporated to dryness
  11. customThe residue is triturated in ethyl ether
  12. filtrationfiltered
  13. customdried in vacuo

출처 및 근거

ORD 기록
ord-8253b3b8bacd438ab0b3414223283023
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08541412B2

연결된 노트

불러오는 중…