Diisopropylethylamine → Methyl 4-[8-(3-bromo-4,5-dichlorobenzyl)-2-oxo-1-oxa-3,8-diazaspiro[4.5]dec-3-yl]benzoate

HRID 402824노트

반응식

HRID 402824 반응식
Cl.[O:2]=[C:3]1[N:7]([C:8]2[CH:17]=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[CH:10][CH:9]=2)[CH2:6][C:5]2([CH2:22][CH2:21][NH:20][CH2:19][CH2:18]2)[O:4]1.[Br:23][C:24]1[CH:29]=[C:28]([CH2:30]Br)[CH:27]=[C:26]([Cl:32])[C:25]=1[Cl:33].CCN(C(C)C)C(C)C>CN(C=O)C>[Br:23][C:24]1[CH:29]=[C:28]([CH:27]=[C:26]([Cl:32])[C:25]=1[Cl:33])[CH2:30][N:20]1[CH2:21][CH2:22][C:5]2([O:4][C:3](=[O:2])[N:7]([C:8]3[CH:17]=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[CH:10][CH:9]=3)[CH2:6]2)[CH2:18][CH2:19]1

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 66764605Methyl 4-(2-oxo-1-oxa-3,8-diazaspiro[4.5]dec-3-yl)benzoate hydrochloride saltHCID 667648061-Bromo-5-(bromomethyl)-2,3-dichlorobenzene

생성물 1

HCID 86685276Methyl 4-[8-(3-bromo-4,5-dichlorobenzyl)-2-oxo-1-oxa-3,8-diazaspiro[4.5]dec-3-yl]benzoate수율 94%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
55 °C

실험 절차

To methyl 4-(2-oxo-1-oxa-3,8-diazaspiro[4.5]dec-3-yl)benzoate hydrochloride salt (50 mg, 0.153 mmol; Example 1, Step 2) and 1-bromo-5-(bromomethyl)-2,3-dichlorobenzene (53.7 mg, 0.168 mmol; from Patent US2007/070805) was added DMF (1.5 mL) and DIPEA (107 μL, 0.612 mmol). The mixture was heated to 55° C. for 2 hours. The mixture was evaporated and the residue was dissolved in saturated aqueous NaHCO3 and then extracted with DCM. The organic layer was evaporated to provide the title compound as a yellow oil (76 mg) that was used without further purification.

후처리

  1. customThe mixture was evaporated
  2. dissolutionthe residue was dissolved in saturated aqueous NaHCO3
  3. extractionextracted with DCM
  4. customThe organic layer was evaporated

출처 및 근거

ORD 기록
ord-6d3a1d35f6a34aca9461a4e4a4a415d3
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08742110B2

반응 노트

불러오는 중…