Diisopropylethylamine → 3-(benzyloxy)-N-(2-fluoro-5-methylphenyl)benzamide

HRID 525832노트

반응식

HRID 525832 반응식
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][CH:17]=1)[C:12]([OH:14])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[F:51][C:52]1[CH:58]=[CH:57][C:56]([CH3:59])=[CH:55][C:53]=1[NH2:54]>CN(C=O)C>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][CH:17]=1)[C:12]([NH:54][C:53]1[CH:55]=[C:56]([CH3:59])[CH:57]=[CH:58][C:52]=1[F:51])=[O:14])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

6

반응물 4

HCID 81531DiisopropylethylamineHCID 2629702-Fluoro-5-methylanilineHCID 3092263-(Benzyloxy)benzoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

생성물 1

HCID 429677573-(benzyloxy)-N-(2-fluoro-5-methylphenyl)benzamide

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a stirred solution of 3-benzyloxy benzoic acid (1.00 g, 4.38 mmol) in 20 ml of anhydrous DMF were added HATU (1.83 g, 4.82 mmol) and DIPEA (1.7 ml, 9.6 mmol). The mixture was stirred at room temperature for 10 minutes, followed by addition of 2-fluoro-5-methylaniline (657 mg, 5.25 mmol). The mixture was heated at 66° C. for 16 hours, cooled to room temperature, and partitioned between EtOAc (100 ml) and 0.5M HCl (200 ml). The organic phase was washed with 0.5M HCl (2×50 ml), saturated NaHCO3 (50 ml) and brine (50 ml), dried over Na2SO4, and evaporated to dryness to afford 3-(benzyloxy)-N-(2-fluoro-5-methylphenyl)benzamide as light brown solid. Yield: 1.5 g, 100%.

후처리

  1. temperatureThe mixture was heated at 66° C. for 16 hours
  2. temperaturecooled to room temperature
  3. custompartitioned between EtOAc (100 ml) and 0.5M HCl (200 ml)
  4. washThe organic phase was washed with 0.5M HCl (2×50 ml), saturated NaHCO3 (50 ml) and brine (50 ml)
  5. dry with materialdried over Na2SO4
  6. customevaporated to dryness

출처 및 근거

ORD 기록
ord-a7858d59bd8c41548840c5253e991840
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09340555B2

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