2-Oxopropanethioamide → 6'-Bromo-4,4-difluoro-5''-methyl-3'H-dispiro[cyclohexane-1,2'-indene-1',2''-imidazole]-4''(3''H)-thione

HRID 539342

Reaktionsgleichung

Reaktionsgleichung von HRID 539342
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][C:7]3([CH2:16][CH2:15][C:14]([F:18])([F:17])[CH2:13][CH2:12]3)[C:8]2=[NH:11])=[CH:4][CH:3]=1.O=[C:20]([CH3:24])[C:21](=[S:23])[NH2:22]>CO>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][C:7]3([C:8]42[NH:22][C:21](=[S:23])[C:20]([CH3:24])=[N:11]4)[CH2:12][CH2:13][C:14]([F:17])([F:18])[CH2:15][CH2:16]3)=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 207652372-Oxopropanethioamide2×HCID 679795136'-bromo-4,4-difluorospiro[cyclohexane-1,2'-inden]-1'(3'H)-imine

Produkt 1

HCID 866672746'-Bromo-4,4-difluoro-5''-methyl-3'H-dispiro[cyclohexane-1,2'-indene-1',2''-imidazole]-4''(3''H)-thioneAusbeute 73 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

6′-Bromo-4,4-difluorospiro[cyclohexane-1,2′-inden]-1′(3′H)-imine (Example 27 Step 2, 418 mg, 1.33 mmol) and 2-oxopropanethioamide (Intermediate 2, 412 mg, 3.99 mmol) were dissolved in dry MeOH (6 mL) and the resulting solution was heated at 60° C. under N2(g) overnight. The reaction mixture was allowed to cool to r.t. A precipitate formed which was filtered off and dried in vacuo, yielding the title compound (387 mg, 73% yield). 1H NMR (500 MHz, DMSO-d6) δ ppm 1.29-1.47 (m, 2 H), 1.49-1.62 (m, 2 H), 1.81-2.08 (m, 4 H), 2.28 (s, 3 H), 3.09 (d, 1 H), 3.15 (d, 1 H), 7.02 (d, 1 H), 7.33 (d, 1 H), 7.53 (d, 1 H), 12.42 (s, 1 H); MS (ES+) m/z 399.0 [M+H]|.

Aufarbeitung

  1. temperatureto cool to r.t
  2. customA precipitate formed which
  3. filtrationwas filtered off
  4. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-49961958bc054064a64d18d7916de2f8
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08865911B2

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