Diisopropylethylamine → HCID 90386391, 화합물

HRID 2170189노트

반응식

HRID 2170189 반응식
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]2=[C:9]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH:10]=[CH:11][N:4]2[N:3]=1.CCN(C(C)C)C(C)C.[N:27]1[CH:32]=[CH:31][CH:30]=[C:29]2[CH2:33][NH:34][CH2:35][C:28]=12>C1COCC1>[Cl:1][C:2]1[N:7]=[C:6]([N:34]2[CH2:33][C:29]3[C:28](=[N:27][CH:32]=[CH:31][CH:30]=3)[CH2:35]2)[C:5]2=[C:9]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH:10]=[CH:11][N:4]2[N:3]=1

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 15194166,7-dihydro-5H-pyrrolo[3,4-b]pyridineHCID 90386287HCID 90386287, 화합물

생성물 1

HCID 90386391HCID 90386391, 화합물수율 44.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

2,4-Dichloro-5-phenylpyrrolo[2,1-f][1,2,4]triazine (50.0 mg, 0.189 mmol) was dissolved in THF (3 mL) and then DIPEA (0.0990 mL, 0.568 mmol) was added, followed by the addition of 6,7-dihydro-5H-pyrrolo[3,4-b]pyridine (0.0270 g, 0.227 mmol). The reaction mixture was stirred at room temperature for 12 h. The reaction mixture was concentrated under reduced pressure and water (5 mL) was added to the resulting residue. The aqueous solution was extracted with EtOAc (2×25 mL). The organic layer was separated, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by CombiFlash (REDISEP®, silica gel, 12 g, 30% EA/petroleum ether) to afford 2-chloro-5-phenyl-4-(5H-pyrrolo[3,4-b]pyridin-6(7H)-yl)pyrrolo[2,1-f][1,2,4]triazine (29.0 mg, 44.0%) as a brown solid. LCMS Condition B-79: retention time 1.70 min, [M+1]=348.0. 1H NMR (400 MHz, DMSO-d6) δ ppm 4.38 (br s, 2H), 4.84 (br s, 2H), 6.80 (d, J=2.8 Hz, 1H), 7.25 (dd, J=7.7 Hz, J=4.9 Hz, 1H), 7.35-7.54 (m, 5H), 7.64 (br s, 1H), 7.90 (d, J=2.7 Hz, 1H), 8.34 (d, J=4.3 Hz, 1H).

후처리

  1. concentrationThe reaction mixture was concentrated under reduced pressure and water (5 mL)
  2. additionwas added to the resulting residue
  3. extractionThe aqueous solution was extracted with EtOAc (2×25 mL)
  4. customThe organic layer was separated
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by CombiFlash (REDISEP®, silica gel, 12 g, 30% EA/petroleum ether)

출처 및 근거

ORD 기록
ord-9ad96029a7014de7b34d67f7a8291668
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09050345B2

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