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

HRID 1847987ノート

反応式

HRID 1847987 の反応式
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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-469087f6565d4f0c81a5a34f931be870
出典データセット
uspto-grants-2015_02
特許番号
US08952058B2

反応ノート

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