3,4-dihydro-2H-pyran → 6-chloro-1-(tetrahydro-2H-pyran-2-yl)-1H-imidazo[4,5-c]pyridine-4-carbonitrile

HRID 2079553ノート

反応式

HRID 2079553 の反応式
[Cl:1][C:2]1[N:7]=[C:6]([C:8]#[N:9])[C:5]2[N:10]=[CH:11][NH:12][C:4]=2[CH:3]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[O:25]1[CH:30]=[CH:29][CH2:28][CH2:27][CH2:26]1>C(OCC)(=O)C>[Cl:1][C:2]1[N:7]=[C:6]([C:8]#[N:9])[C:5]2[N:10]=[CH:11][N:12]([CH:26]3[CH2:27][CH2:28][CH2:29][CH2:30][O:25]3)[C:4]=2[CH:3]=1

参加物

5

反応物 3

HCID 80803,4-dihydro-2H-pyranHCID 521998p-Toluenesulfonic acid monohydrateHCID 451205836-Chloro-1H-imidazo[4,5-C]pyridine-4-carbonitrile

生成物 1

HCID 592183456-chloro-1-(tetrahydro-2H-pyran-2-yl)-1H-imidazo[4,5-c]pyridine-4-carbonitrile

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

反応条件

温度
60 °C

実験手順

6-Chloro-1H-imidazo[4,5-c]pyridine-4-carbonitrile (620 mg) and p-toluenesulfonic acid monohydrate (10 mg) were suspended in ethyl acetate (10 ml) and heated to 60° C. 3,4-Dihydro-2H-pyran (0.48 ml) was added dropwise and the reaction stirred at 60° C. overnight. The reaction was quenched with 5 mL ammonium hydroxide before addition of water (100 mL) and ethyl acetate (200 mL). Organic layer was separated, dried over sodium sulphate and solvent was evaporated under reduced pressure. The crude product was dissolved in a minimum volume of EtOAc and heptane added. The resulting brown solid was collected by filtration to yield 6-chloro-1-(tetrahydro-2H-pyran-2-yl)-1H-imidazo[4,5-c]pyridine-4-carbonitrile (630 mg). 1H NMR (DMSO) δ: 8.92 (s, 1H), 8.30 (s, 1H), 5.80 (d, 1H), 4.05 (m, 1H), 3.75 (m, 1H), 2.19 (m, 1H), 2.11 (m, 1H), 1.62 (m, 4H).

後処理

  1. customThe reaction was quenched with 5 mL ammonium hydroxide before addition of water (100 mL) and ethyl acetate (200 mL)
  2. customOrganic layer was separated
  3. dry with materialdried over sodium sulphate and solvent
  4. customwas evaporated under reduced pressure
  5. dissolutionThe crude product was dissolved in a minimum volume of EtOAc and heptane
  6. additionadded
  7. filtrationThe resulting brown solid was collected by filtration

出典と根拠

ORDレコード
ord-660f1a11aecf4e669c2a5ca4526844d2
出典データセット
uspto-grants-2011_04
特許番号
US07932251B2

反応ノート

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