Tert-Butylamine → 5-(6-Hydroxymethylpyridin-2-yl)-1-(4-methylpiperazin-1-yl)pent-4-yn-1-one

HRID 1172257

반응식

HRID 1172257 반응식
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][OH:9])[N:3]=1.[CH3:10][N:11]1[CH2:16][CH2:15][N:14]([C:17](=[O:22])[CH2:18][CH2:19][C:20]#[CH:21])[CH2:13][CH2:12]1.C(N)(C)(C)C>[Cu]I.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.CN(C=O)C>[OH:9][CH2:8][C:4]1[N:3]=[C:2]([C:21]#[C:20][CH2:19][CH2:18][C:17]([N:14]2[CH2:15][CH2:16][N:11]([CH3:10])[CH2:12][CH2:13]2)=[O:22])[CH:7]=[CH:6][CH:5]=1

참가 물질

7

반응물 3

HCID 6385Tert-ButylamineHCID 3517811(6-Bromopyridin-2-yl)methanolHCID 577138121-(4-Methylpiperazin-1-yl)pent-4-yn-1-one

생성물 1

HCID 595554265-(6-Hydroxymethylpyridin-2-yl)-1-(4-methylpiperazin-1-yl)pent-4-yn-1-one수율 73%

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418397HCID 178418397, 화합물촉매HCID 6228Dimethylformamide용매

반응 조건

온도
80 °C

실험 절차

To a 50 mL round-bottom flask, 484 mg of 2-bromopyridine-6-methanol, 510 mg of 1-(4-methylpiperazin-1-yl)pent-4-yn-1-one, 20 mg of BHT, 162 mg of copper(I) iodide, 118 mg of tetrakis(triphenylphosphine)palladium (0), 375 mg of t-butylamine and 7.5 mL of DMF were added, and the mixture was stirred under argon atmosphere at 80° C. for 6 hours. The DMF was removed under reduced pressure, then saturated aqueous sodium bicarbonate was added thereto, and the mixture was extracted with chloroform. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and then the solvent was removed. The residue was purified by chromatography on silica gel (methylene chloride-methanol-triethylamine=600:20:1) to give 540 mg of 5-(6-hydroxymethylpyridin-2-yl)-1-(4-methylpiperazin-1-yl)pent-4-yn-1-one as a yellow oil.

후처리

  1. customThe DMF was removed under reduced pressure
  2. additionsaturated aqueous sodium bicarbonate was added
  3. extractionthe mixture was extracted with chloroform
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was removed
  7. customThe residue was purified by chromatography on silica gel (methylene chloride-methanol-triethylamine=600:20:1)

출처 및 근거

ORD 기록
ord-719be10f277d43e5a41d592a205b1bf4
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07834002B2

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