Triphenylphosphine → 5-[(4-Fluorophenyl)carbonyl]-2-[(2-methylpyridin-4-yl)methoxy]-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine

HRID 571733

반응식

HRID 571733 반응식
N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:36][C:37]1[CH:42]=[C:41]([CH2:43][OH:44])[CH:40]=[CH:39][N:38]=1.[F:45][C:46]1[CH:51]=[CH:50][C:49]([C:52]([N:54]2[CH2:59][CH2:58][N:57]3[N:60]=[C:61](O)[CH:62]=[C:56]3[CH2:55]2)=[O:53])=[CH:48][CH:47]=1>C1COCC1>[F:45][C:46]1[CH:47]=[CH:48][C:49]([C:52]([N:54]2[CH2:59][CH2:58][N:57]3[N:60]=[C:61]([O:44][CH2:43][C:41]4[CH:40]=[CH:39][N:38]=[C:37]([CH3:36])[CH:42]=4)[CH:62]=[C:56]3[CH2:55]2)=[O:53])=[CH:50][CH:51]=1

참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 97268Di-tert-butyl azodicarboxylateHCID 9942144(2-Methylpyridin-4-yl)methanolHCID 178519627HCID 178519627, 화합물

생성물 1

HCID 727032155-[(4-Fluorophenyl)carbonyl]-2-[(2-methylpyridin-4-yl)methoxy]-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine수율 35.5%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
130 °C

실험 절차

Di-tert-butyl azodicarboxylate (0.138 g, 0.6 mmol) was added to a stirred solution of triphenylphosphine (0.157 g, 0.6 mmol), (2-methylpyridin-4-yl)methanol (0.074 g, 0.6 mmol) and 5-[(4-fluorophenyl)carbonyl]-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazin-2-ol (0.157 g, 0.6 mmol) in THF (3 mL) in a sealed tube and under nitrogen. The mixture was stirred at 130° C. for 20 minutes under microwave irradiation and the solvents were evaporated in vacuo. The crude product was purified by flash column chromatography (silica; 7 M solution of ammonia in methanol in DCM 0/100 to 5/95, twice). The desired fractions were collected, the solvents evaporated in vacuo and the residue triturated with DIPE to yield 5-[(4-fluorophenyl)carbonyl]-2-[(2-methylpyridin-4-yl)methoxy]-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine (0.078 g, 35% yield) as a white solid. C20H19FN4O2. 1H NMR (400 MHz, CDCl3) δ ppm 2.56 (s, 3 H), 4.08 (br. s., 4 H), 4.74 (br. s., 2 H), 5.17 (s, 2 H), 5.52 (br. s., 1 H), 7.10-7.18 (m, 3 H), 7.21 (br. s, 1 H), 7.45-7.52 (m, 2 H), 8.47 (d, J=5.1 Hz, 1 H).

후처리

  1. customthe solvents were evaporated in vacuo
  2. customThe crude product was purified by flash column chromatography (silica
  3. customThe desired fractions were collected
  4. customthe solvents evaporated in vacuo
  5. customthe residue triturated with DIPE

출처 및 근거

ORD 기록
ord-48b4d776c259422cb876f6f6b47b7b98
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09029366B2

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