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Morpholine → 1-{[(R)-5-(4-Cyano-benzyl)-7-(3,5-dichloro-4-fluoro-phenyl)-5-methyl-6-oxo-6,7-dihydro-5H-imidazo[1,2-a]imidazole-3-carbonyl]-amino}-cyclopropanecarboxylic acid

HRID 449160
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 449160
C([O:4][C:5]([C:7]1([NH:10][C:11]([C:13]2[N:17]3[C@@:18]([CH2:32][C:33]4[CH:38]=[CH:37][C:36]([C:39]#[N:40])=[CH:35][CH:34]=4)([CH3:31])[C:19](=[O:30])[N:20]([C:21]4[CH:26]=[C:25]([Cl:27])[C:24]([F:28])=[C:23]([Cl:29])[CH:22]=4)[C:16]3=[N:15][CH:14]=2)=[O:12])[CH2:9][CH2:8]1)=[O:6])C=C.N1CCOCC1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1COCC1>[C:39]([C:36]1[CH:37]=[CH:38][C:33]([CH2:32][C@@:18]2([CH3:31])[N:17]3[C:13]([C:11]([NH:10][C:7]4([C:5]([OH:6])=[O:4])[CH2:8][CH2:9]4)=[O:12])=[CH:14][N:15]=[C:16]3[N:20]([C:21]3[CH:22]=[C:23]([Cl:29])[C:24]([F:28])=[C:25]([Cl:27])[CH:26]=3)[C:19]2=[O:30])=[CH:34][CH:35]=1)#[N:40]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 8083MorpholineHCID 680892731-{[(R)-5-(4-cyano-benzyl)-7-(3,5-dichloro-4-fluoro-phenyl)-5-methyl-6-oxo-6,7-dihydro-5H-imidazol[1,2-a]imidazole-3-carbonyl]-amino}-cyclopropanecarboxylic acid allyl ester

Produkt 1

HCID 673908991-{[(R)-5-(4-Cyano-benzyl)-7-(3,5-dichloro-4-fluoro-phenyl)-5-methyl-6-oxo-6,7-dihydro-5H-imidazo[1,2-a]imidazole-3-carbonyl]-amino}-cyclopropanecarboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397
HCID 178418397, Verbindung
Katalysator
HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

The ester obtained (12.6 g, 22 mmol) was combined with THF (100 mL). Morpholine (18.6 mL, 210 mmol) and Pd(PPh3)4 (500 mg, 0.40 mmol) were added and the reaction was allowed to stir at room temperature for 16 h. The solution was filtered through diatomaceous earth and then concentrated. The residue was diluted with ethyl acetate (150 mL) washed with water (2×50 mL), 1M HCl (2×50 mL), brine (1×50 mL) and then dried (MgSO4), filtered and concentrated. The residue was purified by flash chromatography (silica-gel) using 10-100% ethyl acetate in hexanes to provide 10.4 g of the title compound.

Aufarbeitung

  1. filtrationThe solution was filtered through diatomaceous earth
  2. concentrationconcentrated
  3. additionThe residue was diluted with ethyl acetate (150 mL)
  4. washwashed with water (2×50 mL), 1M HCl (2×50 mL), brine (1×50 mL)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by flash chromatography (silica-gel)

Quellen und Nachweise

ORD-Eintrag
ord-ec8dd4de326f41e69f0efa12e82ac254
Quelldatensatz
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08481750B2

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