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

HRID 539336ノート

反応式

HRID 539336 の反応式
[Br:1][C:2]1[CH:15]=[C:14]2[C:5]([CH2:6][C:7]3([C:13]2=[NH:16])[CH2:12][CH2:11][O:10][CH2:9][CH2:8]3)=[CH:4][CH:3]=1.O=[C:18]([CH3:22])[C:19](=[S:21])[NH2:20]>CO>[Br:1][C:2]1[CH:15]=[C:14]2[C:5]([CH2:6][C:7]3([C:13]42[NH:20][C:19](=[S:21])[C:18]([CH3:22])=[N:16]4)[CH2:12][CH2:11][O:10][CH2:9][CH2:8]3)=[CH:4][CH:3]=1

参加物

4

反応物 2

HCID 207652372-Oxopropanethioamide2 回HCID 679795066-Bromo-2',3',5',6'-tetrahydrospiro[indene-2,4'-pyran]-1(3H)-imine

生成物 1

HCID 866672736'-Bromo-5-methyl-2'',3'',5'',6''-tetrahydro-3'H-dispiro[imidazole-2,1'-indene-2',4''-pyran]-4(3H)-thione収率 125.5%

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-2′,3′,5′,6′-tetrahydrospiro[indene-2,4′-pyran]-1(3H)-imine (Example 25 Step 2, 235 mg, 0.84 mmol) and 2-oxopropanethioamide (Intermediate 2, 173 mg, 1.68 mmol) were taken up in anhydrous MeOH (5 mL) and the resulting mixture was stirred at 60° C. under a nitrogen atmosphere for 3 h. When cooled to r.t. the mixture was concentrated and purified on a silica gel column eluted with 0-50% EtOAc in heptane to give 385 mg (95% yield) of the title compound; 1 H NMR (500 MHz, DMSO-d6) δ ppm 12.40 (br. s, 1 H), 7.53 (dd, 1 H), 7.36 (d, 1 H), 7.03 (d, 1 H), 3.71 (td, 2 H), 3.44 (m, 2 H), 3.15 (m, 2 H), 2.29 (s, 3 H), 1.64 (s, 1 H), 1.55 (s, 1 H), 1.27 (m, 2 H); MS (ES+) m/z 365 [M+H]+.

後処理

  1. temperatureWhen cooled to r.t. the mixture
  2. concentrationwas concentrated
  3. custompurified on a silica gel column
  4. washeluted with 0-50% EtOAc in heptane

出典と根拠

ORDレコード
ord-2eb3f39025f349ab9ed4c3268a017055
出典データセット
uspto-grants-2014_10
特許番号
US08865911B2

反応ノート

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