Diisopropylethylamine → tert-Butyl 2-(5-bromo-1,3,4-thiadiazol-2-yl)-2,7-diazaspiro[3.5]nonane-7-carboxylate

HRID 579355노트

반응식

HRID 579355 반응식
[Br:1][C:2]1[S:3][C:4](Br)=[N:5][N:6]=1.[CH2:8]1[C:11]2([CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]2)[CH2:10][NH:9]1.CCN(C(C)C)C(C)C>O1CCOCC1.O>[Br:1][C:2]1[S:3][C:4]([N:9]2[CH2:8][C:11]3([CH2:12][CH2:13][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:15][CH2:16]3)[CH2:10]2)=[N:5][N:6]=1

참가 물질

6

반응물 3

HCID 81531DiisopropylethylamineHCID 30925302,5-Dibromo-1,3,4-thiadiazoleHCID 24820512tert-Butyl 2,7-diazaspiro[3.5]nonane-7-carboxylate

생성물 1

HCID 86727178tert-Butyl 2-(5-bromo-1,3,4-thiadiazol-2-yl)-2,7-diazaspiro[3.5]nonane-7-carboxylate수율 88%

시약·촉매·용매 2

HCID 962Water용매HCID 312751,4-Dioxane용매

반응 조건

온도
120 °C

실험 절차

A stirred suspension of 2,5-dibromo-1,3,4-thiadiazole (245 mg, 1.004 mmol), tert-butyl 2,7-diazaspiro[3.5]nonane-7-carboxylate (290 mg, 1.105 mmol) and DIPEA (702 μL, 1.02 mmol) in dioxane (2.5 mL) was heated at 120° C. for 1 hour. The reaction mixture was diluted with water (10 mL), extracted with DCM (20 mL), and the organic phase was concentrated onto silica gel. The crude material was purified by flash chromatography using a 24 g silica cartridge running an EtOAc/heptane gradient to afford the title compound as a yellow oil (343 mg, 88% yield). LC-MS: Rt 1.25 min; MS m/z 391.2 [M+2]+ [Method A]. 1H NMR (400 MHz, Chloroform-d) δ 3.87 (s, 4H), 3.34-3.43 (m, 4H), 1.73-1.85 (m, 4H), 1.46 (s, 9H).

후처리

  1. extractionextracted with DCM (20 mL)
  2. concentrationthe organic phase was concentrated onto silica gel
  3. customThe crude material was purified by flash chromatography

출처 및 근거

ORD 기록
ord-f09887549fc84693a457f5acef494764
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09040712B2

반응 노트

불러오는 중…