Sodium Iodide → HCID 56597093, 화합물

HRID 1750138노트

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HRID 1750138 반응식
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH:9]1[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][CH2:18][O:19][C:20]2[CH:21]=[CH:22][C:23]3SC=N[C:24]=3[CH:28]=2)[CH2:11][CH2:10]1.[Na+].[I-].ClC1C(Cl)=CC=CC=1C1C[CH2:43][NH:42][CH2:41][CH2:40]1.C([O-])([O-])=[O:46].[K+].[K+]>CC#N>[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH:9]1[CH2:10][CH2:11][N:12]([CH2:15][CH2:16][CH2:17][CH2:18][O:19][C:20]2[CH:28]=[C:24]3[C:23]([CH2:40][CH2:41][NH:42][C:43]3=[O:46])=[CH:22][CH:21]=2)[CH2:13][CH2:14]1

참가 물질

6

반응물 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 17895683HCID 17895683, 화합물HCID 56597090HCID 56597090, 화합물

생성물 1

HCID 56597093HCID 56597093, 화합물수율 69%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

A mixture of intermediate 21 (103 mg, 0.35 mmol) and NaI (105 mg, 0.7 mmol) in CH3CN was heated to reflux for 30 min and then cooled to rt. Intermediate 47 (142 mg, 0.53 mmol) and anhydrous K2CO3 (194 mg, 1.4 mmol) were added to the mixture. The resulting mixture was heated to reflux and stirred overnight. Precipitated crystals were filtered off and the filtrate was evaporated under reduced pressure. The residue was extracted with EtOAc. The combined EtOAc layers were washed with brine, dried over anhydrous Na2SO4, concentrated in vacuo and purified by flash chromatography on silica gel column (elution with DCM/MeOH 30:1) to give 7-(4-(4-(2,3-dichlorophenyl)piperidin-1-yl)butoxy)-3,4-dihydroisoquinolin-1(2H)-one (compound 33) (108 mg, 69%). 1H NMR (300 MHz, CDCl3): δ 7.58 (d, J=2.1 Hz, 1H), 7.23-7.11 (m, 5H), 7.02-6.99 (m, 1H), 6.05 (s, 1H), 4.05 (t, J=6.0 Hz, 2H), 3.56-3.53 (m, 2H), 3.15-3.06 (m, 3H), 2.93 (t, J=6.6 Hz, 2H), 2.51 (m, 2H), 2.18 (m, 2H), 1.82 (m, 8H). HPLC: 99%, RT 2.746 min. MS (ESI) ink 447.2 [M+H]+. mp: 113-114° C.

후처리

  1. temperaturewas heated
  2. temperatureto reflux for 30 min
  3. temperatureThe resulting mixture was heated
  4. temperatureto reflux
  5. customPrecipitated crystals
  6. filtrationwere filtered off
  7. customthe filtrate was evaporated under reduced pressure
  8. extractionThe residue was extracted with EtOAc
  9. washThe combined EtOAc layers were washed with brine
  10. dry with materialdried over anhydrous Na2SO4
  11. concentrationconcentrated in vacuo
  12. custompurified by flash chromatography on silica gel column (elution with DCM/MeOH 30:1)

출처 및 근거

ORD 기록
ord-992cb2c0475c4d8685eae70e3caead04
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09156822B2

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