Triethylamine → {3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]azetidin-3-yl}acetonitrile

HRID 571548노트

반응식

HRID 571548 반응식
[C:1]([CH2:3][C:4]1([N:15]2[CH:19]=[C:18]([B:20]3[O:24][C:23]([CH3:26])([CH3:25])[C:22]([CH3:28])([CH3:27])[O:21]3)[CH:17]=[N:16]2)[CH2:7][N:6](C(OC(C)(C)C)=O)[CH2:5]1)#[N:2].C(N(CC)CC)C>C(Cl)Cl.Cl.O1CCOCC1>[CH3:27][C:22]1([CH3:28])[C:23]([CH3:25])([CH3:26])[O:24][B:20]([C:18]2[CH:17]=[N:16][N:15]([C:4]3([CH2:3][C:1]#[N:2])[CH2:5][NH:6][CH2:7]3)[CH:19]=2)[O:21]1

참가 물질

6

반응물 2

HCID 8471TriethylamineHCID 67457197tert-butyl 3-(cyanomethyl)-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)azetidine-1-carboxylate

생성물 1

HCID 71143620{3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]azetidin-3-yl}acetonitrile수율 85%

시약·촉매·용매 3

HCID 313Hydrochloric Acid용매HCID 6344Dichloromethane용매HCID 312751,4-Dioxane용매

실험 절차

A mixture of tert-butyl 3-(cyanomethyl)-3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]azetidine-1-carboxylate (1.5 g, 3.9 mmol) (Example 40, Step 1) in methylene chloride (15 mL) and 4.0 M hydrogen chloride in dioxane (3.9 mL) was stirred at room temperature over weekend. The mixture was treated with triethylamine (1 mL), and the volatiles were removed under reduced pressure. The residue was purified by flash chromatography on a silica gel column with methanol in methylene chloride (0-5%) to afford the desired product (0.95 g, 85%). LCMS (M+H)+: m/z=289.2.

후처리

  1. customthe volatiles were removed under reduced pressure
  2. customThe residue was purified by flash chromatography on a silica gel column with methanol in methylene chloride (0-5%)

출처 및 근거

ORD 기록
ord-87ff0e21117d48f588b3022fc8f50c27
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09023840B2

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