StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

Hydrochloric Acid → 7-[4-(3-Amino-oxetan-3-yl)-phenyl]-8-phenyl-2H-9-oxa-1,2,3a-triaza-cyclopenta[a]naphthalene-3,6-dione

HRID 1037327
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1037327
[O:1]=[C:2]1[N:6]2[CH:7]=[CH:8][C:9]3[C:10](=[O:38])[C:11]([C:21]4[CH:26]=[CH:25][C:24]([C:27]5([NH:31]S(C(C)(C)C)=O)[CH2:30][O:29][CH2:28]5)=[CH:23][CH:22]=4)=[C:12]([C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=4)[O:13][C:14]=3[C:5]2=[N:4][N:3]1COCC[Si](C)(C)C.Cl.O1CCOCC1>CO>[NH2:31][C:27]1([C:24]2[CH:25]=[CH:26][C:21]([C:11]3[C:10](=[O:38])[C:9]4[CH:8]=[CH:7][N:6]5[C:2](=[O:1])[NH:3][N:4]=[C:5]5[C:14]=4[O:13][C:12]=3[C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:22][CH:23]=2)[CH2:30][O:29][CH2:28]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 866710502-Methyl-propane-2-sulfinic acid (3-{-4-[3,6-dioxo-8-phenyl-2-(2-trimethylsilanyl-ethoxymethyl)-2,6-dihydro-3H-9-oxa-1,2,3a-triaza-cyclopenta[a]naphthalen-7-yl]-phenyl}-oxetan-3-yl)-amide

Produkt 1

HCID 510300457-[4-(3-Amino-oxetan-3-yl)-phenyl]-8-phenyl-2H-9-oxa-1,2,3a-triaza-cyclopenta[a]naphthalene-3,6-dioneAusbeute 52 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a stirred solution of 2-methyl-propane-2-sulfinic acid (3-{-4-[3,6-dioxo-8-phenyl-2-(2-trimethylsilanyl-ethoxymethyl)-2,6-dihydro-3H-9-oxa-1,2,3a-triaza-cyclopenta[a]naphthalen-7-yl]-phenyl}-oxetan-3-yl)-amide (46 mg, 0.07 mmol) in MeOH (6 mL) was added a solution of HCl in dioxane (4 M, 0.14 mL, 0.56 mmol) at RT. After 1 h, the reaction mixture was evaporated to dryness. The residue was suspended in DCM (5 mL), cooled in an ice bath, and TFA (1 mL) was added. The mixture was stirred at RT for 1 h before evaporating to dryness. The residue was dissolved in MeOH and loaded on to a 2 g SCX-2 cartridge. The cartridge was washed with MeOH before eluting with 2 M NH3 in MeOH solution. The eluent was collected and evaporated. The resulting residue was subjected to flash chromatography (SiO2, gradient 10 to 30% 2 M NH3/MeOH in DCM) to afford the title compound (15 mg, 52%) as a pale yellow solid. 1H NMR (400 MHz, DMSO-d6): δ 7.81 (d, J=7.2 Hz, 1H), 7.54 (d, J=8.3 Hz, 2H), 7.44-7.36 (m, 5H), 7.22 (d, J=8.2 Hz, 2H), 6.97 (d, J=7.2 Hz, 1H), 4.70 (d, J=6.1 Hz, 2H), 4.66 (d, J=6.1 Hz, 2H). LCMS (Method E): RT=2.35 min, [M+H]+=427.

Aufarbeitung

  1. customthe reaction mixture was evaporated to dryness
  2. temperaturecooled in an ice bath
  3. additionTFA (1 mL) was added
  4. custombefore evaporating to dryness
  5. dissolutionThe residue was dissolved in MeOH
  6. washThe cartridge was washed with MeOH
  7. washbefore eluting with 2 M NH3 in MeOH solution
  8. customThe eluent was collected
  9. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-8d91f066e6994d13b2416d137440425b
Quelldatensatz
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08546376B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion