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

HRID 539327

反応式

HRID 539327 の反応式
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][C:7]3([CH2:16][CH2:15][CH:14]([O:17][CH3:18])[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)[CH2:16][CH2:15][CH:14]([O:17][CH3:18])[CH2:13][CH2:12]3)=[CH:4][CH:3]=1

参加物

4

反応物 2

HCID 207652372-Oxopropanethioamide2 回HCID 67979447Trans-6'-bromo-4-methoxyspiro[cyclohexane-1,2'-inden]-1'(3'H)-imine

生成物 1

HCID 866672716'-Bromo-4-methoxy-5''-methyl-3'H-dispiro[cyclohexane-1,2'-indene-1',2''-imidazole]-4''(3''H)-thione収率 64.5%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
60 °C

実験手順

6′-Bromo-4-methoxyspiro[cyclohexane-1,2′-inden]-1′(3′H)-imine (Example 19 Step 2, 1.41 g, 4.57 mmol) and 2-oxopropanethioamide (Intermediate 2, 1.42 g, 13.7 mmol) were dissolved in dry MeOH (30 mL) and the resulting solution was heated at 60° C. under an atmosphere of nitrogen. After 15 h the reaction was allowed to cool to r.t. A precipitate had formed which was filtered off and dried in vacuo, yielding the title compound (1.16 g, 64% yield) as a mixture of isomers. 1H NMR (500 MHz, DMSO-d6) δ ppm 1.18 (m, 4 H), 1.47 (m, 2 H), 1.87 (m, 2 H), 2.27 (m, 3 H), 3.03 (m, 3 H), 3.20 (s, 3 H), 6.98 (d, 1 H), 7.34 (d, 1 H), 7.51 (dd, 1 H); MS (APCI+) m/z 394 [M+H]+.

後処理

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

出典と根拠

ORDレコード
ord-df6f11c05b444b5a9c6b15eb064f6b04
出典データセット
uspto-grants-2014_10
特許番号
US08865911B2

関連ノート

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