Diisopropylethylamine → (1-Methanesulfonyl-1,2,3,4-tetrahydro-quinolin-7-yl)-[7-(6-methoxy-pyridin-3-yl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl]-amine

HRID 1262218Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1262218
[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([C:9]2[N:17]3[C:12]([CH:13]=[N:14][C:15](OS(C(F)(F)F)(=O)=O)=[N:16]3)=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.C(N(CC)C(C)C)(C)C.[CH3:35][S:36]([N:39]1[C:48]2[C:43](=[CH:44][CH:45]=[C:46]([NH2:49])[CH:47]=2)[CH2:42][CH2:41][CH2:40]1)(=[O:38])=[O:37]>CN(C)C=O.CCOC(C)=O>[CH3:35][S:36]([N:39]1[C:48]2[C:43](=[CH:44][CH:45]=[C:46]([NH:49][C:15]3[N:14]=[CH:13][C:12]4=[CH:11][CH:10]=[C:9]([C:6]5[CH:7]=[N:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=5)[N:17]4[N:16]=3)[CH:47]=2)[CH2:42][CH2:41][CH2:40]1)(=[O:38])=[O:37]

Komponenten

6

Edukt 3

HCID 81531DiisopropylethylamineHCID 91252911-(Methylsulfonyl)-1,2,3,4-tetrahydroquinolin-7-amineHCID 86661684Trifluoro-methanesulfonic acid 7-(6-methoxy-pyridin-3-yl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl ester

Produkt 1

HCID 66712559(1-Methanesulfonyl-1,2,3,4-tetrahydro-quinolin-7-yl)-[7-(6-methoxy-pyridin-3-yl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl]-amineAusbeute 47,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Trifluoro-methanesulfonic acid 7-(6-methoxy-pyridin-3-yl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl ester (95.0 mg, 0.254 mmol) was dissolved in N,N-dimethylformamide (3.00 mL). N,N-diisopropylethylamine (133 uL, 0.761 mmol) was added followed by 1-methanesulfonyl-1,2,3,4-tetrahydro-quinolin-7-ylamine (80.4 mg, 0.355 mmol) and the reaction was stirred overnight. The reaction was taken up in EtOAc (25 mL) and washed three times with water (25 mL). The organic layer was dried over sodium sulfate, filtered, and concentrated under reduced pressure. Purification by silica gel chromatography using a gradient of 0-70% EtOAc/hex as the eluting solvent to obtain the title compound as a yellow solid (54 mg, 47%). m.p.=202-203° C.; LCMS (m/e) 451 (M+H); 1H-NMR (d6-DMSO, 400 MHz) δ 9.46 (s, 1H), 8.98 (s, 1H), 8.89 (s, 1H), 8.53 (dd, 1H, J=2.2 and 8.7 Hz), 7.81 (s, 1H), 7.53 (d, 1H, J=8.4 Hz), 7.19 (d, 1H, J=4.7 Hz), 7.10 (d, 1H, J=8.4 Hz), 7.02-6.93 (m, 2H), 3.93 (s, 3H), 3.74-3.68 (m, 2H), 2.99 (s, 3H), 2.79-2.72 (m, 2H), 1.97-1.88 (m, 2H).

Aufarbeitung

  1. washwashed three times with water (25 mL)
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customPurification by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-5d2e900929284c809afcad778408a45d
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08471005B2

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