Triethylamine → N,N-dimethyl-3-(4-((6-phenyl-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methoxy)pyridin-3-yl)prop-2-yn-1-amine

HRID 1513723

반응식

HRID 1513723 반응식
I[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[N:14]2[N:15]=[C:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH:17]=[CH:18][C:13]2=[N:12][N:11]=1.[CH3:25][N:26]([CH3:30])[CH2:27][C:28]#[CH:29].C(N(CC)CC)C>C1COCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cu]I>[CH3:25][N:26]([CH3:30])[CH2:27][C:28]#[C:29][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[N:14]2[N:15]=[C:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH:17]=[CH:18][C:13]2=[N:12][N:11]=1

참가 물질

7

반응물 3

HCID 8471TriethylamineHCID 81643N,N-DimethylpropargylamineHCID 576911573-((3-Iodopyridin-4-yloxy)methyl)-6-phenyl-[1,2,4]triazolo[4,3-b]pyridazine

생성물 1

HCID 57691024N,N-dimethyl-3-(4-((6-phenyl-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methoxy)pyridin-3-yl)prop-2-yn-1-amine

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418397HCID 178418397, 화합물촉매HCID 8028Tetrahydrofuran용매

반응 조건

온도
75 °C

실험 절차

Tetrakis(triphenylphosphine)palladium(0) (14.4 mg, 12.5 μmol) was added to a suspension of 3-((3-iodopyridin-4-yloxy)methyl)-6-phenyl-[1,2,4]triazolo[4,3-b]pyridazine (107 mg, 249 μmol) and 1-dimethylamino-2-propyne (80.4 μl, 748 μmol) in THF (0.6 mL) and triethylamine (591 μl, 4238 μmol) at RT. Copper(i) iodide, 99.999% (4.75 mg, 24.9 μmol) was added and the reaction mixture was stirred at 75° C. (oil bath) for ˜75 min. The reaction mixture was cooled at RT, concentrated in vacuo. Purification by MPLC (ISCO, CH2Cl2/MeOH: 100/0 to 90/10) afforded the title compound. MS m/z=385.1 [M+H]+. Calc'd for C, 22; H, 20; N, 6; O, : 384.44

후처리

  1. temperatureThe reaction mixture was cooled at RT
  2. concentrationconcentrated in vacuo
  3. customPurification by MPLC (ISCO, CH2Cl2/MeOH: 100/0 to 90/10)

출처 및 근거

ORD 기록
ord-42411ee82bee41fc9f0e9be6f823c673
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08217177B2

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