1-Butanol → 1-(4-(4-(4-(4-(Aminomethyl)piperidin-1-yl)-5-fluoropyrimidin-2-ylamino)phenyl)piperazin-1-yl)ethanone

HRID 2281386노트

반응식

HRID 2281386 반응식
Cl[C:2]1[N:7]=[C:6](Cl)[C:5]([F:9])=[CH:4][N:3]=1.C([N:12]([CH2:15][CH3:16])[CH2:13][CH3:14])C.[NH2:17][C:18]1[CH:23]=[CH:22][C:21]([N:24]2[CH2:29][CH2:28][N:27]([C:30](=[O:32])[CH3:31])[CH2:26][CH2:25]2)=[CH:20][CH:19]=1.C(O)CCC.[CH3:38][C:39]#[N:40]>>[NH2:40][CH2:39][CH:38]1[CH2:14][CH2:13][N:12]([C:6]2[C:5]([F:9])=[CH:4][N:3]=[C:2]([NH:17][C:18]3[CH:19]=[CH:20][C:21]([N:24]4[CH2:25][CH2:26][N:27]([C:30](=[O:32])[CH3:31])[CH2:28][CH2:29]4)=[CH:22][CH:23]=3)[N:7]=2)[CH2:15][CH2:16]1

참가 물질

6

반응물 5

HCID 2631-ButanolHCID 6342AcetonitrileHCID 8471TriethylamineHCID 2507052,4-Dichloro-5-fluoropyrimidineHCID 7362691-[4-(4-Aminophenyl)piperazin-1-yl]ethan-1-one

생성물 1

HCID 444673191-(4-(4-(4-(4-(Aminomethyl)piperidin-1-yl)-5-fluoropyrimidin-2-ylamino)phenyl)piperazin-1-yl)ethanone

실험 절차

A mixture of 2,4-dichloro-5-fluoropyrimidine (167 mg, 1.00 mmol), 4-N-Boc-aminomethyl piperidine (214 mg, 1.00 mmol) and triethylamine (0.300 mL, 2.15 mmol) in CH3CN (4 mL) was stirred at room temperature for 20 h. It was concentrated in vacuo. The residue was dissolved in nBuOH (6 mL). 2 mL of the nBuOH solution was taken, to which 1-(4-(4-aminophenyl)piperazin-1-yl)ethanone (108 mg, 0.49 mmol) was added. The solution was stirred at 116° C. for 20 h. nBuOH was removed in vacuo. The residue was dissolved in TFA (2 mL). After being stirred at room temperature for 2 h, TFA was removed in vacuo. The residue was purified by HPLC to give the titled compound (43 mg). MS 428.6 (M+H); UV 206.8, 265.8 nm.

후처리

  1. concentrationIt was concentrated in vacuo
  2. dissolutionThe residue was dissolved in nBuOH (6 mL)
  3. additionwas added
  4. customwas removed in vacuo
  5. dissolutionThe residue was dissolved in TFA (2 mL)
  6. stirringAfter being stirred at room temperature for 2 h
  7. customTFA was removed in vacuo
  8. customThe residue was purified by HPLC

출처 및 근거

ORD 기록
ord-657bdb18136f47e28fdc88b5e1b3b521
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09139581B2

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