Diisopropylethylamine → HCID 90386391、化合物

HRID 2170189ノート

反応式

HRID 2170189 の反応式
[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

参加物

5

反応物 3

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

生成物 1

HCID 90386391HCID 90386391、化合物収率 44.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-9ad96029a7014de7b34d67f7a8291668
出典データセット
uspto-grants-2015_06
特許番号
US09050345B2

反応ノート

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