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

HRID 579355ノート

反応式

HRID 579355 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
120 °C

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-f09887549fc84693a457f5acef494764
出典データセット
uspto-grants-2015_05
特許番号
US09040712B2

反応ノート

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