Potassium Carbonate → tert-butyl 4-(1-(3-methoxy-4-((6-methoxypyridin-3-yl)methoxy)benzyl)-1H-benzo[d]imidazol-5-yl)piperidine-1-carboxylate

HRID 706434노트

반응식

HRID 706434 반응식
[OH:1][C:2]1[CH:30]=[CH:29][C:5]([CH2:6][N:7]2[C:11]3[CH:12]=[CH:13][C:14]([CH:16]4[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]4)=[CH:15][C:10]=3[N:9]=[CH:8]2)=[CH:4][C:3]=1[O:31][CH3:32].C(=O)([O-])[O-].[K+].[K+].Cl[CH2:40][C:41]1[CH:42]=[CH:43][C:44]([O:47][CH3:48])=[N:45][CH:46]=1>CN(C)C=O.[Cl-].[NH4+]>[CH3:32][O:31][C:3]1[CH:4]=[C:5]([CH:29]=[CH:30][C:2]=1[O:1][CH2:40][C:41]1[CH:46]=[N:45][C:44]([O:47][CH3:48])=[CH:43][CH:42]=1)[CH2:6][N:7]1[C:11]2[CH:12]=[CH:13][C:14]([CH:16]3[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:27])([CH3:28])[CH3:26])=[O:23])[CH2:18][CH2:17]3)=[CH:15][C:10]=2[N:9]=[CH:8]1

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 137528915-(Chloromethyl)-2-methoxypyridineHCID 118114035tert-butyl 4-(1-(4-hydroxy-3-methoxybenzyl)-1H-benzo[d]imidazol-5-yl)piperidine-1-carboxylate

생성물 1

HCID 118113962tert-butyl 4-(1-(3-methoxy-4-((6-methoxypyridin-3-yl)methoxy)benzyl)-1H-benzo[d]imidazol-5-yl)piperidine-1-carboxylate수율 82%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매2회HCID 25517Ammonium Chloride용매

실험 절차

To a stirred solution of tert-butyl 4-(1-(4-hydroxy-3-methoxybenzyl)-1H-benzo[d]imidazol-5-yl)piperidine-1-carboxylate (0.51 g, 1.16 mmol) in N,N-dimethylformamide (5 mL) was added potassium carbonate (0.32 g, 2.32 mmol). The mixture was treated with a solution of 5-(chloromethyl)-2-methoxypyridine (219 mg, 1.39 mmol) in N,N-dimethylformamide (2 mL) added dropwise. The mixture was stirred at room temperature. After 16 h, the mixture was diluted with saturated ammonium chloride solution (20 mL) and extracted with ethyl acetate (3×30 mL). The combined organic layers were washed with brine (3×10 mL), dried over sodium sulfate, filtered and concentrated to afford 0.53 g (82%) of tert-butyl 4-(1-(3-methoxy-4-((6-methoxypyridin-3-yl)methoxy)benzyl)-1H-benzo[d]imidazol-5-yl)piperidine-1-carboxylate as a light yellow solid.

후처리

  1. additionadded dropwise
  2. extractionextracted with ethyl acetate (3×30 mL)
  3. washThe combined organic layers were washed with brine (3×10 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-ba4902c2731d46149dca8efa19dc8853
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09174986B2

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