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

HRID 2079553노트

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HRID 2079553 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

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온도
60 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-660f1a11aecf4e669c2a5ca4526844d2
출처 데이터셋
uspto-grants-2011_04
특허 번호
US07932251B2

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