Triethylamine → Tert-butyl(6-(2-(triethylsilyl)ethynyl)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methylcarbamate

HRID 219093

반응식

HRID 219093 반응식
Cl[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([CH2:11][NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[N:9][N:10]=2)[N:7]=1.[CH2:20]([Si:22]([CH2:27][CH3:28])([CH2:25][CH3:26])[C:23]#[CH:24])[CH3:21].C(N(CC)CC)C>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(Cl)Cl.[Cu](I)I.C(#N)C>[C:15]([O:14][C:13](=[O:19])[NH:12][CH2:11][C:8]1[N:6]2[N:7]=[C:2]([C:21]#[C:20][Si:22]([CH2:27][CH3:28])([CH2:25][CH3:26])[CH2:23][CH3:24])[CH:3]=[CH:4][C:5]2=[N:10][N:9]=1)([CH3:18])([CH3:17])[CH3:16]

참가 물질

7

반응물 3

HCID 8471TriethylamineHCID 637947(Triethylsilyl)acetyleneHCID 57691389tert-Butyl ((6-chloro-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methyl)carbamate

생성물 1

HCID 57691160Tert-butyl(6-(2-(triethylsilyl)ethynyl)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methylcarbamate

시약·촉매·용매 3

HCID 83717Copper iodide촉매HCID 178418807HCID 178418807, 화합물촉매HCID 6342Acetonitrile용매

실험 절차

A 1 L-round-bottomed flask flushed with argon was charged with tert-butyl (6-chloro-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methylcarbamate (12.00 g, 42.3 mmol), Pd(dppf)Cl2-CH2Cl2 adduct (3.45 g, 4.23 mmol), copper iodide (2.01 g, 10.6 mmol) at room temperature. Acetonitrile (400 mL) was added followed by triethyl(ethynyl)silane (37.9 ml, 211 mmol). Upon stirring the reaction mixture turned dark red. Triethylamine (177 ml, 1269 mmol) was added via cannula over five minutes. The first drops resulted in a change of color to light yellow/orange. At the end of the addition, the reaction mixture was dark red again. After stirring at 50° C. for one hour, the mixture was cooled to room temperature and concentrated in vacuo. Purification by MPLC (ISCO, EtOAc/MeOH: 100/0 to 90/10) afforded the desired product. The material was taken forward without further purification. MS m/z=388.3 [M+1]+. Calc'd for C19H29N5O2Si: 387.2.

후처리

  1. customA 1 L-round-bottomed flask flushed with argon
  2. customThe first drops resulted in a change of color to light yellow/orange
  3. additionAt the end of the addition
  4. stirringAfter stirring at 50° C. for one hour
  5. concentrationconcentrated in vacuo
  6. customPurification by MPLC (ISCO, EtOAc/MeOH: 100/0 to 90/10)

출처 및 근거

ORD 기록
ord-1c06deba54cc4e058ee06469c7a1e1da
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08198448B2

연결된 노트

불러오는 중…