1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 4-(1-(3-Amino-4-methylbenzoyl)azepan-4-yl)benzonitrile

HRID 541218Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 541218
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5]([OH:7])=O.[NH:12]1[CH2:18][CH2:17][CH2:16][CH:15]([C:19]2[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[CH:21][CH:20]=2)[CH2:14][CH2:13]1.OC1C2N=NNC=2C=CC=1.C(N=C=NCCCN(C)C)C.C(N(CC)C(C)C)(C)C>C(OCC)(=O)C.CN(C=O)C>[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5]([N:12]1[CH2:18][CH2:17][CH2:16][CH:15]([C:19]2[CH:20]=[CH:21][C:22]([C:23]#[N:24])=[CH:25][CH:26]=2)[CH2:14][CH2:13]1)=[O:7]

Komponenten

8

Edukt 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 755683-Amino-4-methylbenzoic acidHCID 81531DiisopropylethylamineHCID 682889074-(Azepan-4-yl)benzonitrile2×HCID 178418300HCID 178418300, Verbindung

Produkt 1

HCID 682889154-(1-(3-Amino-4-methylbenzoyl)azepan-4-yl)benzonitrileAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a 4-mL vial was added 3-amino-4-methylbenzoic acid (27 mg, 0.18 mmol, 1.0 equiv), 4-(azepan-4-yl)benzonitrile (compound 40.4, 40 mg, 0.2 mmol, 1.1 equiv), hydroxybenzotriazole (39 mg of 20 wt % H2O, 0.23 mmol, 1.3 equiv), 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide (44 mg, 0.23 mmol, 1.3 equiv), DMF (1 mL) and N,N-diisopropylethylamine (93 μL, 0.54 mmol, 3.0 equiv). The mixture was stirred at room temperature for 4 hours then diluted into ethyl acetate (10 mL) and washed with brine (10 mL). The aqueous was extracted with ethyl acetate (3 mL) and the combined organics were washed with brine (10 mL), 1 M NaH2PO4 (5 mL) and brine (10 mL). The organics were dried (Na2SO4), filtered and concentrated to obtain the title compound as a brown solid (45 mg, 74%). m/z (ES+) 334 (M+H)+.

Aufarbeitung

  1. washwashed with brine (10 mL)
  2. extractionThe aqueous was extracted with ethyl acetate (3 mL)
  3. washthe combined organics were washed with brine (10 mL), 1 M NaH2PO4 (5 mL) and brine (10 mL)
  4. dry with materialThe organics were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-32b2a822a30f4affaec8519f8ecc72f2
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08871790B2

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