Sodium triacetoxyborohydride → 2-(2-(4-fluorophenyl)oxazol-4-yl)-2-methyl-N-(3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzyl)propan-1-amine

HRID 1397363노트

반응식

HRID 1397363 반응식
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[F:15][C:16]([F:31])([F:30])[C:17]1[O:21][N:20]=[C:19]([C:22]2[CH:23]=[C:24]([CH:27]=[CH:28][CH:29]=2)[CH:25]=O)[N:18]=1.[F:32][C:33]1[CH:38]=[CH:37][C:36]([C:39]2[O:40][CH:41]=[C:42]([C:44]([CH3:48])([CH3:47])[CH2:45][NH2:46])[N:43]=2)=[CH:35][CH:34]=1>ClCCCl>[F:32][C:33]1[CH:34]=[CH:35][C:36]([C:39]2[O:40][CH:41]=[C:42]([C:44]([CH3:48])([CH3:47])[CH2:45][NH:46][CH2:25][C:24]3[CH:27]=[CH:28][CH:29]=[C:22]([C:19]4[N:18]=[C:17]([C:16]([F:31])([F:30])[F:15])[O:21][N:20]=4)[CH:23]=3)[N:43]=2)=[CH:37][CH:38]=1

참가 물질

5

반응물 3

HCID 5049666Sodium triacetoxyborohydrideHCID 185454733-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzaldehydeHCID 673230862-(2-(4-Fluorophenyl)oxazol-4-yl)-2-methylpropan-1-amine

생성물 1

HCID 673249692-(2-(4-fluorophenyl)oxazol-4-yl)-2-methyl-N-(3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzyl)propan-1-amine수율 18%

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

실험 절차

Sodiumtriacetoxy borohydride (197 mg, 0.9 mmol) was added to a solution of 3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzaldehyde (150 mg, 0.62 mmol) and 2-(2-(4-fluorophenyl)oxazol-4-yl)-2-methylpropan-1-amine (150 mg, 0.64 mmol) in dry DCE (2 mL) at 0° C. under nitrogen atmosphere and stirred at room temperature for 8 h (monitored by TLC, petroleum ether/EtOAc 6:4). Reaction mixture was carefully quenched with 10% NaHCO3 solution and the organic product was extracted with EtOAc. The combined extracts were washed with brine, dried over anhydrous Na2SO, and concentrated under reduced pressure. The crude product was purified by column chromatography (silica 60-120 mesh, eluant 10-15% EtOAc in petroleum ether) to get 2-(2-(4-fluorophenyl)oxazol-4-yl)-2-methyl-N-(3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzyl)propan-1-amine (50 mg, yield 18%). 1H NMR (400 MHz, MeOD) δ 8.01 (m, 2H), 7.96-7.92 (m, 3H), 7.67 (s, 1H), 7.54-7.52 (m, 1H), 7.49-7.45 (m, 1H), 7.20-7.15 (m, 1H), 3.82 (s, 2H), 2.76 (s, 2H), 1.32 (s, 6H). MS (ESI) m/z: Calculated for C23H20F4N4O2: 460.15. found: 461.2 (M+H)+.

후처리

  1. customReaction mixture
  2. customwas carefully quenched with 10% NaHCO3 solution
  3. extractionthe organic product was extracted with EtOAc
  4. washThe combined extracts were washed with brine
  5. dry with materialdried over anhydrous Na2SO
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified by column chromatography (silica 60-120 mesh, eluant 10-15% EtOAc in petroleum ether)

출처 및 근거

ORD 기록
ord-60af69429260443fa230edf7989e9bfc
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08901156B2

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