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N-methyl-2-pyrrolidone → [2-Methoxy-4-(4-methyl-piperazin-1-yl)-phenyl]-[7-(6-methoxy-pyridin-3-yl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl]-amine

HRID 1261885
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1261885
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][N:21]([CH3:24])[CH2:20][CH2:19]4)=[CH:14][C:13]=3[O:25][CH3:26])=[N:9]2)=[CH:4][CH:3]=1.[CH3:27][O:28][C:29]1C=[C:33]([N:35]2CCN(C)CC2)[CH:32]=[CH:31][C:30]=1N.BrC1N2C(C=NC(S(C)=O)=N2)=CC=1.CN1CCCC1=O>>[CH3:26][O:25][C:13]1[CH:14]=[C:15]([N:18]2[CH2:23][CH2:22][N:21]([CH3:24])[CH2:20][CH2:19]2)[CH:16]=[CH:17][C:12]=1[NH:11][C:8]1[N:7]=[CH:6][C:5]2=[CH:4][CH:3]=[C:2]([C:32]3[CH:33]=[N:35][C:29]([O:28][CH3:27])=[CH:30][CH:31]=3)[N:10]2[N:9]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 4

HCID 13387N-methyl-2-pyrrolidoneHCID 201362532-Methoxy-4-(4-methylpiperazin-1-yl)anilineHCID 580713077-Bromo-2-(methylsulfinyl)pyrrolo[2,1-f][1,2,4]triazineHCID 66710919(7-Bromo-pyrrolo[2,1-f][1,2,4]triazin-2-yl)-[2-methoxy-4-(4-methyl-piperazin-1-yl)-phenyl]-amine

Produkt 1

HCID 66711356
[2-Methoxy-4-(4-methyl-piperazin-1-yl)-phenyl]-[7-(6-methoxy-pyridin-3-yl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl]-amine

Reaktionsbedingungen

Temperatur
145 °C

Versuchsvorschrift

(7-Bromo-pyrrolo[2,1-f][1,2,4]triazin-2-yl)-[2-methoxy-4-(4-methyl-piperazin-1-yl)-phenyl]-amine: Into a 30 mL vial, [A] 2-Methoxy-4-(4-methyl-piperazin-1-yl)-phenylamine (1.08 g, 0.00490 mol), [B] 7-Bromo-2-methanesulfinyl-pyrrolo[2,1-f][1,2,4]triazine (0.580 g, 0.00223 mol) and N-Methylpyrrolidinone (3.50 mL, 0.0363 mol) were added. The reaction mixture was heated at 145° C. for 2.5 hours. The solvent was removed under vacuum to give a solid. The solid was partitioned with water and DCM. The organic was separated, washed with Brine and dried over sodium sulfate. The solid was filtered and washed with DCM. The solvent was removed under vacuum. The desired product was isolated via ISCO column chromatography with DCM and MeOH as eluant (3 to 10% methanol). The collected fractions afforded (7-Bromo-pyrrolo[2,1-f][1,2,4]triazin-2-yl)-[2-methoxy-4-(4-methyl-piperazin-1-yl)-phenyl]-amine as a yellow solid (0.58 g, 62%). NMR 1H (DSMO-d6)-8.83 (s, 1H), 8.03 (d, 1H, J=8.76 Hz), 7.75 (s, 1H), 6.92 (d, 1H, J=4.58 Hz), 6.86 (d, 1H, J=4.68 Hz), 6.67 (d, 1H, J=2.24 Hz), 6.49 (dd, 1H, JJ=2.32, 6.44 Hz), 3.85 (s, 3H), 3.12 (t, 4H, J=4.64 Hz), 2.46 (t, 4H, J=4.84 Hz), 2.22 (s, 3H)

Aufarbeitung

  1. customThe solvent was removed under vacuum
  2. customto give a solid
  3. customThe solid was partitioned with water and DCM
  4. customThe organic was separated
  5. washwashed with Brine
  6. dry with materialdried over sodium sulfate
  7. filtrationThe solid was filtered
  8. washwashed with DCM
  9. customThe solvent was removed under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-a80237c0528a4e8a9b025c7069c8e648
Quelldatensatz
uspto-grants-2013_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08471005B2

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