Water → methyl 1-[(3,4-dimethylphenyl)methyl]-2-methyl-6-(4-morpholinyl)-1H-benzimidazole-4-carboxylate

HRID 1749604

반응식

HRID 1749604 반응식
[CH3:1][C:2]1[NH:6][C:5]2[C:7]([C:17]([O:19][CH3:20])=[O:18])=[CH:8][C:9]([N:11]3[CH2:16][CH2:15][O:14][CH2:13][CH2:12]3)=[CH:10][C:4]=2[N:3]=1.Cl[CH2:22][C:23]1[CH:28]=[CH:27][C:26]([CH3:29])=[C:25]([CH3:30])[CH:24]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH3:30][C:25]1[CH:24]=[C:23]([CH2:22][N:3]2[C:4]3[CH:10]=[C:9]([N:11]4[CH2:12][CH2:13][O:14][CH2:15][CH2:16]4)[CH:8]=[C:7]([C:17]([O:19][CH3:20])=[O:18])[C:5]=3[N:6]=[C:2]2[CH3:1])[CH:28]=[CH:27][C:26]=1[CH3:29]

참가 물질

6

반응물 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 660183,4-Dimethylbenzyl chlorideHCID 178498372HCID 178498372, 화합물

생성물 1

HCID 67102198methyl 1-[(3,4-dimethylphenyl)methyl]-2-methyl-6-(4-morpholinyl)-1H-benzimidazole-4-carboxylate수율 76%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
80 °C

실험 절차

To a solution of methyl 2-methyl-5-(4-morpholinyl)-1H-benzimidazole-7-carboxylate prepared as described in Example 26, step d (0.22 g, 0.799 mmol) in N,N-Dimethylformamide (DMF) (10 mL) was added in 4-(chloromethyl)-1,2-dimethylbenzene (0.185 g, 1.199 mmol) and potassium carbonate (0.331 g, 2.397 mmol). The resulting reaction mixture was stirred at 80° C. for 3 h. It was cooled to room temperature and poured into water (30 mL). The mixture was extracted with EtOAc (50 mL×3). The combined organic phases were washed with brine (50 mL) and concentrated. The crude material was subjected to normal phase purification (0˜40% EtOAc/Hexane) then (0˜1% MeOH/DCM) to give the product (0.24 g, 76%). MS(ES+) m/e 394.0 [M+H]+.

후처리

  1. customThe resulting reaction mixture
  2. temperatureIt was cooled to room temperature
  3. extractionThe mixture was extracted with EtOAc (50 mL×3)
  4. washThe combined organic phases were washed with brine (50 mL)
  5. concentrationconcentrated
  6. customThe crude material was subjected to normal phase purification (0˜40% EtOAc/Hexane)

출처 및 근거

ORD 기록
ord-35f2bac9b63e4c8e9535691008c8c814
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09156797B2

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