Triethylamine → 2-(4-((S)-4-benzyl-2-isopropylpiperazin-1-yl)-7-methylquinazolin-2-yl)phenol

HRID 2079322노트

반응식

HRID 2079322 반응식
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([CH3:12])=[CH:9][CH:10]=2)[N:5]=[C:4]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[OH:19])[N:3]=1.[CH2:20]([N:27]1[CH2:32][CH2:31][NH:30][C@@H:29]([CH:33]([CH3:35])[CH3:34])[CH2:28]1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(N(CC)CC)C>CN(C=O)C>[CH2:20]([N:27]1[CH2:32][CH2:31][N:30]([C:2]2[C:11]3[C:6](=[CH:7][C:8]([CH3:12])=[CH:9][CH:10]=3)[N:5]=[C:4]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[OH:19])[N:3]=2)[C@@H:29]([CH:33]([CH3:35])[CH3:34])[CH2:28]1)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 17750438(3S)-1-Benzyl-3-(propan-2-yl)piperazineHCID 1361050322-(4-Chloro-7-methylquinazolin-2-yl)-phenol

생성물 1

HCID 1361215792-(4-((S)-4-benzyl-2-isopropylpiperazin-1-yl)-7-methylquinazolin-2-yl)phenol수율 64%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
85 °C

실험 절차

To a solution of 2-(4-chloro-7-methylquinazolin-2-yl)phenol (200 mg, 0.74 mmol) in 10 mL DMF was added (S)-1-benzyl-3-isopropylpiperazine followed by the addition of triethylamine (206 μL). The reaction was heated at 85° C. for two hours. The reaction was quenched with water after cooling it to room temperature. The aqueous layer was extracted twice with CH2Cl2, and the combined extracts were dried over MgSO4, filtered, and concentrated. The reaction was purified via silica gel chromatography using 1:1 hexanes:CH2Cl2 solvent system to yield 2-(4-((S)-4-benzyl-2-isopropylpiperazin-1-yl)-7-methylquinazolin-2-yl)phenol (230 mg, 64%). LC/MS: m/z 453.5 (M+H)+ at 2.61 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

후처리

  1. customThe reaction was quenched with water
  2. temperatureafter cooling it to room temperature
  3. extractionThe aqueous layer was extracted twice with CH2Cl2
  4. dry with materialthe combined extracts were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe reaction was purified via silica gel chromatography

출처 및 근거

ORD 기록
ord-3564d8aaf9524175b8d1455d245b8361
출처 데이터셋
uspto-grants-2011_04
특허 번호
US07928107B2

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