Ethylene Glycol → (4-Morpholin-4-yl-phenyl)-(7-phenylsulfanyl-pyrrolo[2,1-f][1,2,4]triazin-2-yl)-amine

HRID 1261896노트

반응식

HRID 1261896 반응식
Br[C:2]1[N:10]2[C:5]([CH:6]=[N:7][C:8]([NH:11][C:12]3[CH:17]=[CH:16][C:15]([N:18]4[CH2:23][CH2:22][O:21][CH2:20][CH2:19]4)=[CH:14][CH:13]=3)=[N:9]2)=[CH:4][CH:3]=1.CC(C)([O-])C.[Na+].C(O)CO.CN(C)C=O.[C:39]1([SH:45])[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1>[Cu]I>[N:18]1([C:15]2[CH:16]=[CH:17][C:12]([NH:11][C:8]3[N:7]=[CH:6][C:5]4=[CH:4][CH:3]=[C:2]([S:45][C:39]5[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=5)[N:10]4[N:9]=3)=[CH:13][CH:14]=2)[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1

참가 물질

7

반응물 5

HCID 174Ethylene GlycolHCID 6228DimethylformamideHCID 7969ThiophenolHCID 23676156Sodium t-butoxideHCID 54578326(7-Bromo-pyrrolo[2,1-f][1,2,4]triazin-2-yl)-(4-morpholin-4-yl-phenyl)-amine

생성물 1

HCID 66710894(4-Morpholin-4-yl-phenyl)-(7-phenylsulfanyl-pyrrolo[2,1-f][1,2,4]triazin-2-yl)-amine

시약·촉매·용매 1

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매

반응 조건

온도
120 °C

실험 절차

Into a sealed tube was added (7-Bromo-pyrrolo[2,1-f][1,2,4]triazin-2-yl)-(4-morpholin-4-yl-phenyl)-amine (0.125 g, 0.334 mmol), Sodium tert-butoxide (96.4 mg, 1.00 mmol), Copper(I) iodide (6.4 mg, 0.033 mmol), 1,2-Ethanediol (37.4 uL, 0.671 mmol), N,N-Dimethylformamide (4.7 mL, 6.0E1 mmol), and finally Benzenethiol (51.4 uL, 0.501 mmol). The reaction was heated at 120° C. overnight. The reaction was partitioned with DCM and water. The organic was separated, washed with Brine, and dried over magnesium sulfate. The solid was filtered and washed with DCM. The solvent was removed under vacuum. The product was isolated via ISCO column chromatography with DCM and methanol as eluant (0 to 10% methanol) the collected fractions afforded (4-Morpholin-4-yl-phenyl)-(7-phenylsulfanyl-pyrrolo[2,1-f][1,2,4]triazin-2-yl)-amine an orange solid (72 mg, 53%). MP 143-145° C. LCMS (E/I+) 404.17 (M+H). NMR 1H (DSMO-d6)-9.33 (s, 1H), 8.97 (s, 1H), 7.45 (d, 2H, J=9.05 Hz), 7.30 (t, 2H, J=7.57 Hz), 7.18 (t, 1H, J=7.29), 7.12 (d, 2H, J=7.37 Hz), 7.01 (d, 1H, J=4.40 Hz), 6.93 (d, 1H, J=4.60 Hz), 6.75 (d, 2H, J=9.05 Hz), 3.73 (t, 4H, J=4.48 Hz), 3.00 (t, 4H, J=4.72 Hz).

후처리

  1. customThe reaction was partitioned with DCM and water
  2. customThe organic was separated
  3. washwashed with Brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationThe solid was filtered
  6. washwashed with DCM
  7. customThe solvent was removed under vacuum
  8. customThe product was isolated via ISCO column chromatography with DCM and methanol as eluant (0 to 10% methanol) the collected fractions

출처 및 근거

ORD 기록
ord-2b787b5903e0472491251e948a60c605
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08471005B2

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