Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate → 3-[1-[3,5-Dimethyl-4-(4-morpholin-4-yl-piperidine-1-carbonyl)-1H-pyrrol-2-yl]-meth-(Z)-ylidene]4-(3-fluoro-phenyl)-1,3-dihydro-indol-2-one

HRID 983170Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 983170
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:16]=[CH:15][CH:14]=[C:13]3[C:9]=2/[C:10](=[CH:18]/[C:19]2[NH:23][C:22]([CH3:24])=[C:21]([C:25]([OH:27])=O)[C:20]=2[CH3:28])/[C:11](=[O:17])[NH:12]3)[CH:5]=[CH:6][CH:7]=1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.[NH:56]1[CH2:61][CH2:60][CH:59]([N:62]2[CH2:67][CH2:66][O:65][CH2:64][CH2:63]2)[CH2:58][CH2:57]1.[Li+].[Cl-]>CN(C=O)C.C(Cl)(Cl)Cl.C(O)(C)C>[CH3:28][C:20]1[C:21]([C:25]([N:56]2[CH2:61][CH2:60][CH:59]([N:62]3[CH2:67][CH2:66][O:65][CH2:64][CH2:63]3)[CH2:58][CH2:57]2)=[O:27])=[C:22]([CH3:24])[NH:23][C:19]=1/[CH:18]=[C:10]1\[C:11](=[O:17])[NH:12][C:13]2[C:9]\1=[C:8]([C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=1)[CH:16]=[CH:15][CH:14]=2

Komponenten

7

Edukt 4

HCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 433294Lithium ChlorideHCID 7957244-MorpholinopiperidineHCID 697413865-[4-(3-Fluoro-phenyl)-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-2,4-dimethyl-1H-pyrrole-3-carboxylic acid

Produkt 1

HCID 600615833-[1-[3,5-Dimethyl-4-(4-morpholin-4-yl-piperidine-1-carbonyl)-1H-pyrrol-2-yl]-meth-(Z)-ylidene]4-(3-fluoro-phenyl)-1,3-dihydro-indol-2-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 21906603Chloroform isopropyl alcoholLösungsmittel

Versuchsvorschrift

5-[4-(3-Fluoro-phenyl)-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-2,4-dimethyl-1H-pyrrole-3-carboxylic acid (1 eq.) and BOP (1.25 eq.) were suspended in DMF (5 mL) at rt and TEA (2.4 eq.) was added. After 15 mina, to the homogenous reaction mixture was added 4-piperidin-4-yl-morpholine (1.25 eq.) all at once. After stirring for 2 days, the reaction was added to a mixture of chloroform-isopropanol (5:1) and 5% aq. LiCl. The organic layer was separated, washed with 5% aq. LiCl (2×), 1M aq. NaOH (3×), brine, dried and concentrated. The residue was purified to give the titled compound

Aufarbeitung

  1. customThe organic layer was separated
  2. washwashed with 5% aq. LiCl (2×), 1M aq. NaOH (3×), brine
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified

Quellen und Nachweise

ORD-Eintrag
ord-a2edc60f9ff54e23974e2874294d4a64
Quelldatensatz
uspto-grants-2005_03
Patentnummer
US06861418B2

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