Potassium Carbonate → 6-((5,6-dimethoxy-1H-benzo[d]imidazol-1-yl)methyl)-2-(methylthio)benzo[d]oxazole

HRID 1847987노트

반응식

HRID 1847987 반응식
CS(O[CH2:6][C:7]1[CH:17]=[CH:16][C:10]2[N:11]=[C:12]([S:14][CH3:15])[O:13][C:9]=2[CH:8]=1)(=O)=O.ClCC1C=CC2N=C(SC)OC=2C=1.[CH3:31][O:32][C:33]1[C:41]([O:42][CH3:43])=[CH:40][C:36]2[N:37]=[CH:38][NH:39][C:35]=2[CH:34]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:43][O:42][C:41]1[C:33]([O:32][CH3:31])=[CH:34][C:35]2[N:39]([CH2:6][C:7]3[CH:17]=[CH:16][C:10]4[N:11]=[C:12]([S:14][CH3:15])[O:13][C:9]=4[CH:8]=3)[CH:38]=[N:37][C:36]=2[CH:40]=1

참가 물질

6

반응물 4

HCID 11430Potassium CarbonateHCID 6012215,6-DimethoxybenzimidazoleHCID 86681015(2-(Methylthio)benzo[d]oxazol-6-yl)methyl methanesulfonateHCID 866810166-(Chloromethyl)-2-(methylthio)benzo[d]oxazole

생성물 1

HCID 866810146-((5,6-dimethoxy-1H-benzo[d]imidazol-1-yl)methyl)-2-(methylthio)benzo[d]oxazole

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a stirred solution of a 9:1 mixture of (2-(methylthio)benzo[d]oxazol-6-yl)methyl methanesulfonate and 6-(chloromethyl)-2-(methylthio)benzo[d]oxazole (1.45 g) from Step 1 of this Example and 5,6-dimethoxybenzimidazole (945 mg, 5.31 mmol) in anhydrous DMF (10 mL) at rt was added solid K2CO3 (1.47 g, 10.62 mmol). The mixture was stirred at rt for 3 h. The mixture was partitioned between water and DCM. The organic layer was separated and washed with water. The organic layer was separated, dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by silica gel flash chromatography eluting with 100% DCM to 10% MeOH in DCM to afford 6-((5,6-dimethoxy-1H-benzo[d]imidazol-1-yl)methyl)-2-(methylthio)benzo[d]oxazole (430 mg) as a solid. 1H NMR (300 MHz, DMSO-d6) δ 8.20 (s, 1H), 7.66 (m, 1H), 7.60 (d, J=9.0 Hz, 1H), 7.32 (dd, J=9.0, 3.0 Hz, 1H), 7.19 (s, 2H), 5.53 (s, 2H), 3.76 (s, 6H), 2.73 (s, 3H). LCMS (ESI) m/z 356 (M+H)+.

후처리

  1. customat rt
  2. customThe mixture was partitioned between water and DCM
  3. customThe organic layer was separated
  4. washwashed with water
  5. customThe organic layer was separated
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by silica gel flash chromatography
  10. washeluting with 100% DCM to 10% MeOH in DCM

출처 및 근거

ORD 기록
ord-469087f6565d4f0c81a5a34f931be870
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08952058B2

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