Sodium Iodide → N-[1-[3-(3-cyanophenyloxy)propan-1-yl]piperidin-4-yl]-5-thia-1,8b-diazaacenaphthylene-4-carboxamide

HRID 1978529노트

반응식

HRID 1978529 반응식
Cl[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]([CH:11]=[CH:12][CH:13]=1)[C:9]#[N:10].C(#N)C.Cl.Cl.[NH:19]1[CH2:24][CH2:23][CH:22]([NH:25][C:26]([C:28]2[S:38][C:37]3[N:39]4[C:30](=[CH:31][N:32]=[C:33]4[CH:34]=[CH:35][CH:36]=3)[CH:29]=2)=[O:27])[CH2:21][CH2:20]1.[I-].[Na+]>C(N(CC)CC)C>[C:9]([C:8]1[CH:7]=[C:6]([O:5][CH2:4][CH2:3][CH2:2][N:19]2[CH2:20][CH2:21][CH:22]([NH:25][C:26]([C:28]3[S:38][C:37]4[N:39]5[C:30](=[CH:31][N:32]=[C:33]5[CH:34]=[CH:35][CH:36]=4)[CH:29]=3)=[O:27])[CH2:23][CH2:24]2)[CH:13]=[CH:12][CH:11]=1)#[N:10]

참가 물질

6

반응물 4

HCID 5238Sodium IodideHCID 6342AcetonitrileHCID 219940813-(3-Chloropropoxy)benzonitrileHCID 21994154N-(piperidin-4-yl)-5-thia-1,8b-diazaacenaphthylene-4-carboxamide dihydrochloride

생성물 1

HCID 21994000N-[1-[3-(3-cyanophenyloxy)propan-1-yl]piperidin-4-yl]-5-thia-1,8b-diazaacenaphthylene-4-carboxamide수율 57.4%

시약·촉매·용매 1

HCID 8471Triethylamine용매

실험 절차

3-(3-Chloropropan-1-yl)oxybenzonitrile (503 mg) was added, at room temperature, to an acetonitrile solution (20 ml) of N-(piperidin-4-yl)-5-thia-1,8b-diazaacenaphthylene-4-carboxamide dihydrochloride (800 mg), 1,8b-diazabicyclo[5.4.0]-7-undecene (662 mg), triethylamine (1.09 g) and sodium iodide (285 mg). The mixture was heated under reflux for 6.5 hours under nitrogen atmosphere. The reaction mixture was concentrated under reduced pressure. To the concentrate was added water, which was subjected to extraction with chloroform. The extract solution was washed with a saturated aqueous saline solution, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The concentrate was purified by means of a silica gel chromatography (ethyl acetate/methanol=2/1) to afford the object compound (565 mg, 57%) as reddish purple crystals.

후처리

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 6.5 hours under nitrogen atmosphere
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. additionTo the concentrate was added water, which
  5. extractionwas subjected to extraction with chloroform
  6. washThe extract solution was washed with a saturated aqueous saline solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe concentrate was purified by means of a silica gel chromatography (ethyl acetate/methanol=2/1)

출처 및 근거

ORD 기록
ord-beb0b1dd9f44477e9310a949873ca747
출처 데이터셋
uspto-grants-2001_05
특허 번호
US06235731B1

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