N'-(2-Amino-7-(2-(4-(2,4-difluorophenyl)piperazin-1-yl)ethyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)furan-2-carbohydrazide → 7-(2-(4-(2,4-difluorophenyl)piperazin-1-yl)ethyl)-2-(furan-2-yl)-7H-pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5-amine

HRID 2239815

Reaktionsgleichung

Reaktionsgleichung von HRID 2239815
[NH2:1][C:2]1[N:3]=[C:4]([NH:27][NH:28][C:29]([C:31]2[O:32][CH:33]=[CH:34][CH:35]=2)=O)[C:5]2[CH:10]=[CH:9][N:8]([CH2:11][CH2:12][N:13]3[CH2:18][CH2:17][N:16]([C:19]4[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:20]=4[F:26])[CH2:15][CH2:14]3)[C:6]=2[N:7]=1>C[Si](N[Si](C)(C)C)(C)C>[F:26][C:20]1[CH:21]=[C:22]([F:25])[CH:23]=[CH:24][C:19]=1[N:16]1[CH2:17][CH2:18][N:13]([CH2:12][CH2:11][N:8]2[C:6]3[N:7]=[C:2]([NH2:1])[N:27]4[N:28]=[C:29]([C:31]5[O:32][CH:33]=[CH:34][CH:35]=5)[N:3]=[C:4]4[C:5]=3[CH:10]=[CH:9]2)[CH2:14][CH2:15]1

Komponenten

3

Edukt 1

HCID 68414926N'-(2-Amino-7-(2-(4-(2,4-difluorophenyl)piperazin-1-yl)ethyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)furan-2-carbohydrazide

Produkt 1

HCID 250207657-(2-(4-(2,4-difluorophenyl)piperazin-1-yl)ethyl)-2-(furan-2-yl)-7H-pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5-amine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 13838HexamethyldisilazaneLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

The title B compound, N′-(2-amino-7-(2-(4-(2,4-difluorophenyl)piperazin-1-yl)ethyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)furan-2-carbohydrazide (53 mg, 0.11 mmol) is dissolved in 0.5 mL of HMDS and 0.5 mL in BSA. The mixture is heated at 120° C. for 16 h, then cooled to RT and evaporated to dryness. The residue is stirred in a mixture of DCM and 6N aqueous HCl for an hour at RT, then the pH is adjusted to 9 with 1M aqueous NaOH. The organic phase is collected and the aqueous phase extracted with additional DCM. The combined organic extracts are dried (Na2SO4), filtered and evaporated. Purification of the residue by flash chromatography, eluting with 3% MeOH in DCM affords 7-(2-(4-(2,4-difluorophenyl)piperazin-1-yl)ethyl)-2-(furan-2-yl)-7H-pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5-amine as an off-white solid: LC/MS (M+1=465.2). 1H NMR (CDCl3) δ 3.01 (m, 2H), 3.25 (m, 2H), 3.39 (m, 2H), 3.52 (m, 4H), 4.86 (t, 2H, J=6.6 Hz), 5.76 (br s, 2H), 6.54 (dd, 1H, J=1.8 Hz and 3.4 Hz), 6.8-6.72 (m, 3H), 7.11 (dd, 1H, J=4.6 Hz), 7.19 (m, 2H), 7.57 (t, 1H, J=0.8 Hz).

Aufarbeitung

  1. temperaturecooled to RT
  2. customevaporated to dryness
  3. customThe organic phase is collected
  4. extractionthe aqueous phase extracted with additional DCM
  5. dry with materialThe combined organic extracts are dried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated
  8. customPurification of the residue by flash chromatography
  9. washeluting with 3% MeOH in DCM

Quellen und Nachweise

ORD-Eintrag
ord-6428fb202f9242ff9c9970d7e77c6fed
Quelldatensatz
uspto-grants-2010_05
Patentnummer
US07723343B2

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