Phthalimide → HCID 69248953, Verbindung

HRID 1037550Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1037550
[CH:1]1([C:4]2[C:12]([N:13]([CH2:18][CH2:19][CH2:20]O)[S:14]([CH3:17])(=[O:16])=[O:15])=[CH:11][C:10]3[C:6](=[C:7]([C:36]([NH:38][CH3:39])=[O:37])[N:8]([C:22]4[CH:27]=[CH:26][C:25]([NH:28][C:29]5[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=5)=[CH:24][CH:23]=4)[N:9]=3)[CH:5]=2)[CH2:3][CH2:2]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:59]1(=[O:69])[NH:63][C:62](=[O:64])[C:61]2=[CH:65][CH:66]=[CH:67][CH:68]=[C:60]12.N(C(OC(C)C)=O)=NC(OC(C)C)=O.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[CH:1]1([C:4]2[C:12]([N:13]([CH2:18][CH2:19][CH2:20][N:63]3[C:59](=[O:69])[C:60]4[C:61](=[CH:65][CH:66]=[CH:67][CH:68]=4)[C:62]3=[O:64])[S:14]([CH3:17])(=[O:16])=[O:15])=[CH:11][C:10]3[C:6](=[C:7]([C:36]([NH:38][CH3:39])=[O:37])[N:8]([C:22]4[CH:27]=[CH:26][C:25]([NH:28][C:29]5[CH:30]=[CH:31][C:32]([F:35])=[CH:33][CH:34]=5)=[CH:24][CH:23]=4)[N:9]=3)[CH:5]=2)[CH2:3][CH2:2]1

Komponenten

7

Edukt 5

HCID 6809Phthalimide2×HCID 11776Triphenylphosphine2×HCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 5363146Diisopropyl azodicarboxylateHCID 675177915-Cyclopropyl-2-{4-[(4-fluorophenyl)amino]phenyl}-6-[(3-hydroxypropyl)(methylsulfonyl)amino]-N-methyl-2H-indazole-3-carboxamide

Produkt 1

HCID 69248953HCID 69248953, VerbindungAusbeute 326,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of compound (ii) (5 mg, 0.009 mmol), triphenylphosphine (3.6 mg, 0.014 mmol) and phthalimide (2.0 mg, 0.014 mmol) in THF (0.5 mL) was added diisopropyl azodicarboxylate (2.7 μL, 0.014 mmol) at 0° C. After the mixture had been stirred at RT for 3.5 h, more triphenylphosphine (3.6 mg, 0.014 mmol), phthalimide (2.0 mg, 0.014 mmol) and DIAD (2.7 μL, 0.014 mmol) were added and stirring was continued at RT for a further 40 min. The solvent was removed in vacuo and the residue was purified by preparative LCMS (5-50-100% ACN in 0.1% aqueous formic acid) to afford 5-cyclopropyl-6-[3-(1,3-dioxoisoindolin-2-yl)propyl-methylsulfonyl-amino]-2-[4-(4-fluoroanilino)phenyl]-N-methyl-indazole-3-carboxamide (iii) as a white solid (20 mg, 81%).

Aufarbeitung

  1. stirringstirring
  2. waitwas continued at RT for a further 40 min
  3. customThe solvent was removed in vacuo
  4. customthe residue was purified by preparative LCMS (5-50-100% ACN in 0.1% aqueous formic acid)

Quellen und Nachweise

ORD-Eintrag
ord-8ca34f4bf575488a866f72b1f841972f
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08546389B2

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