2-Methyl-5-(6-nitrobenzoxazol-2-yl)-1-(tetrahydropyran-4-yl)benzimidazole → 2-Methyl-5-(6-aminobenzoxazol-2-yl)-1-(tetrahydropyran-4-yl)benzimidazole

HRID 74218노트

반응식

HRID 74218 반응식
[CH3:1][C:2]1[N:6]([CH:7]2[CH2:12][CH2:11][O:10][CH2:9][CH2:8]2)[C:5]2[CH:13]=[CH:14][C:15]([C:17]3[O:18][C:19]4[CH:25]=[C:24]([N+:26]([O-])=O)[CH:23]=[CH:22][C:20]=4[N:21]=3)=[CH:16][C:4]=2[N:3]=1.[H][H]>[Pd].CO>[CH3:1][C:2]1[N:6]([CH:7]2[CH2:8][CH2:9][O:10][CH2:11][CH2:12]2)[C:5]2[CH:13]=[CH:14][C:15]([C:17]3[O:18][C:19]4[CH:25]=[C:24]([NH2:26])[CH:23]=[CH:22][C:20]=4[N:21]=3)=[CH:16][C:4]=2[N:3]=1

참가 물질

5

반응물 2

HCID 674986292-Methyl-5-(6-nitrobenzoxazol-2-yl)-1-(tetrahydropyran-4-yl)benzimidazoleHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 674987622-Methyl-5-(6-aminobenzoxazol-2-yl)-1-(tetrahydropyran-4-yl)benzimidazole수율 40.2%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 887Methanol용매

실험 절차

2-Methyl-5-(6-nitrobenzoxazol-2-yl)-1-(tetrahydropyran-4-yl)benzimidazole (see Working Example 47-2) (135 mg, 0.357 mmol) was added to methanol (20 mL) containing palladium/carbon (Pd: 10%, 0.06 g), hydrogen was substituted in by successively reducing the pressure and purging with hydrogen gas 3 times, and this was stirred at room temperature for 2.5 hours. After substituting in nitrogen, the insoluble material was filtered off through a Celite layer (20 mm thickness), and this same layer was washed with methanol (20 mL, 3 times). The filtrate was combined with the wash solutions and the solvent was distilled out at reduced pressure, the residue obtained was purified by silica gel column chromatography to yield the title compound (50 mg, 40.2% yield) as brown crystals.

후처리

  1. custompurging with hydrogen gas 3 times
  2. filtrationthe insoluble material was filtered off through a Celite layer (20 mm thickness)
  3. washthis same layer was washed with methanol (20 mL, 3 times)
  4. distillationthe solvent was distilled out at reduced pressure
  5. customthe residue obtained
  6. customwas purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-833e975568284f908dc7e5138b34377f
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08829035B2

반응 노트

불러오는 중…