Acetaldehyde → 2-Methyl-5-(4-methylbenzoxazol-2-yl)-1-(tetrahydropyran-4-yl)benzimidazole

HRID 74215노트

반응식

HRID 74215 반응식
[O:1]1[CH2:6][CH2:5][CH:4]([NH:7][C:8]2[CH:14]=[CH:13][C:12]([C:15]3[O:16][C:17]4[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=4[N:19]=3)=[CH:11][C:9]=2[NH2:10])[CH2:3][CH2:2]1.[CH:24](=O)[CH3:25].OOS([O-])=O.[K+].[C:33](=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O>[CH3:24][C:25]1[N:7]([CH:4]2[CH2:3][CH2:2][O:1][CH2:6][CH2:5]2)[C:8]2[CH:14]=[CH:13][C:12]([C:15]3[O:16][C:17]4[CH:23]=[CH:22][CH:21]=[C:20]([CH3:33])[C:18]=4[N:19]=3)=[CH:11][C:9]=2[N:10]=1

참가 물질

7

반응물 4

HCID 177AcetaldehydeHCID 11430Potassium CarbonateHCID 23707502Potassium hydroxy sulfiteHCID 674988065-(Benzoxazol-2-yl)-2-(tetrahydropyran-4-yl)aminoaniline

생성물 1

HCID 674988722-Methyl-5-(4-methylbenzoxazol-2-yl)-1-(tetrahydropyran-4-yl)benzimidazole수율 20.4%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

To a solution of 2-(2-(tetrahydropyran-4-yl)aminoanilin-5-yl)benzoxazole (see Working Example 46-2) (0.56 g, 1.7 mmol) in dimethylformamide (5 mL) containing water (0.18 mL) was added an aqueous solution of acetaldehyde (approx. 90%, 90 mg, 1.8 mmol) and oxone (0.69 mg, 1.1 mmol), and this was stirred at room temperature for 3 hours. After the reaction was complete, aqueous potassium carbonate solution was added, this was filtered and washed with water. The crystals obtained were purified by silica gel column chromatography to yield the title compound (123 mg, 20.4% yield) as light brown crystals.

후처리

  1. filtrationthis was filtered
  2. washwashed with water
  3. customThe crystals obtained
  4. customwere purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-764065c8d4984caeb5f455023038785f
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08829035B2

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