Cesium carbonate → 2-(1-(6-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)-2-methylpyrimidin-4-yl)azetidin-3-yl)-1-methyl-1H-benzo[d]imidazole

HRID 2202819ノート

反応式

HRID 2202819 の反応式
Cl[C:2]1[CH:7]=[C:6]([N:8]2[C:12]([CH3:13])=[N:11][C:10]([CH3:14])=[N:9]2)[N:5]=[C:4]([CH3:15])[N:3]=1.[NH:16]1[CH2:19][CH:18]([C:20]2[N:24]([CH3:25])[C:23]3[CH:26]=[CH:27][CH:28]=[CH:29][C:22]=3[N:21]=2)[CH2:17]1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[CH3:14][C:10]1[N:11]=[C:12]([CH3:13])[N:8]([C:6]2[N:5]=[C:4]([CH3:15])[N:3]=[C:2]([N:16]3[CH2:19][CH:18]([C:20]4[N:24]([CH3:25])[C:23]5[CH:26]=[CH:27][CH:28]=[CH:29][C:22]=5[N:21]=4)[CH2:17]3)[CH:7]=2)[N:9]=1

参加物

5

反応物 3

HCID 10796Cesium carbonateHCID 624817454-chloro-6-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)-2-methylpyrimidineHCID 894881762-(azetidin-3-yl)-1-methyl-1H-1,3-benzodiazole

生成物 1

HCID 715508042-(1-(6-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)-2-methylpyrimidin-4-yl)azetidin-3-yl)-1-methyl-1H-benzo[d]imidazole収率 78%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

Intermediate 2 (0.15 g, 0.67 mmol), Intermediate 1 (0.13 g, 0.67 mmol), and Cs2CO3 (0.66 g, 2.01 mmol) were suspended in DMF (6.7 mL) in a microwave vial. The vial was then capped and heated in the microwave at 100° C. for 30 min. After cooling to room temperature, the reaction was filtered and the filtrate was purified by reverse phase chromatography (acetonitrile/water/0.1% TFA). The fractions containing the product were partitioned between EtOAc and saturated NaHCO3. The organic layer was washed with brine, dried over Na2SO4 and concentrated to provide Example 1 (0.17 g, 78%) as a white solid. 1H NMR: (500 MHz, CD3OD) δ 7.63 (d, J=8 Hz, 1H), 7.5 (d, J=8 Hz, 1H), 7.28 (m, 2H), 6.66 (s, 1H), 4.66 (m, 2H), 4.53 (m, 3H), 3.83 (s, 3H), 2.84 (s, 3H), 2.51 (s, 3H), 2.36 (s, 3H). MS: m/z=375.4 (M+H).

後処理

  1. customThe vial was then capped
  2. temperatureAfter cooling to room temperature
  3. filtrationthe reaction was filtered
  4. customthe filtrate was purified by reverse phase chromatography (acetonitrile/water/0.1% TFA)
  5. additionThe fractions containing the product
  6. customwere partitioned between EtOAc and saturated NaHCO3
  7. washThe organic layer was washed with brine
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrated

出典と根拠

ORDレコード
ord-7d7907bc92004eb39c43b875041a2121
出典データセット
uspto-grants-2016_06
特許番号
US09365562B2

反応ノート

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