Diethylamine → HCID 59596689, 화합물

HRID 2264829노트

반응식

HRID 2264829 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[F:16])=[CH:4][N:3]=1.[CH3:17][C:18]([O:21][C:22]([NH:24][C@@H:25]([CH2:30][C:31]#[CH:32])[C:26]([O:28][CH3:29])=[O:27])=[O:23])([CH3:20])[CH3:19].C(NCC)C>C(OCC)C.[Cu](I)I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:20][C:18]([O:21][C:22]([NH:24][C@@H:25]([CH2:30][C:31]#[C:32][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[F:16])=[CH:4][N:3]=1)[C:26]([O:28][CH3:29])=[O:27])=[O:23])([CH3:17])[CH3:19]

참가 물질

7

반응물 3

HCID 8021DiethylamineHCID 11817013(S)-Methyl 2-((tert-butoxycarbonyl)amino)pent-4-ynoateHCID 59596668HCID 59596668, 화합물

생성물 1

HCID 59596689HCID 59596689, 화합물수율 40%

시약·촉매·용매 3

HCID 83717Copper iodide촉매HCID 178418476HCID 178418476, 화합물촉매HCID 3283Diethyl Ether용매

실험 절차

To a solution of 2-bromo-5-{[(2-fluorophenyl)methyl]oxy}pyridine (D82, 0.60 g, 2.13 mmol), methyl (2S)-2-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-4-pentynoate (D64, 1.20 g, 5.30 mmol), synthesized with an analogous procedure to the one described hereinabove, and diethylamine (1.10 ml, 10.65 mmol) in diethyl ether (20 ml) were added copper iodide (0.042 g, 0.22 mmol) and PdCl2(PPh3)2 (0.077 g, 0.11 mmol) and the mixture was stirred for three hours at room temperature. The reaction was quenched with a saturated solution of ammonium chloride diluted with water and extracted with diethyl ether. The organic layer was dried (Na2SO4) filtered and evaporated. The residue was purified by chromatography on silica gel using cyclohexane/ethyl acetate (9:1 to 8:2) to afford the title compound as a yellow solid (0.36 g, 40%). Rt (HPLC): 5.64 min; MS: (ES/+) m/z: 429 [MH]+ C23H25FN2O5 requires 428; 1H NMR (400 MHz, CDCl3) δ (ppm): 8.28-8.39 (m, 1H); 7.44-7.53 (m, 1H); 7.32-7.41 (m, 2H); 7.16-7.25 (m, 2H); 7.08-7.16 (m, 1H); 5.37-5.55 (m, 1H); 5.19 (s, 2H); 4.46-4.66 (m, 1H); 3.81 (s, 3H); 2.91-3.07 (m, 2H); 1.47 (s, 9H).

후처리

  1. customThe reaction was quenched with a saturated solution of ammonium chloride
  2. additiondiluted with water
  3. extractionextracted with diethyl ether
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by chromatography on silica gel

출처 및 근거

ORD 기록
ord-742370fe5aa845d6be58d590a62bd5b1
출처 데이터셋
uspto-grants-2010_12
특허 번호
US07855218B2

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