Triethylamine → 1-(t-Butoxycarbonyl)-4-([1,2,4]triazolo[4,3-a]pyridin-3-yl)piperidine

HRID 1068227노트

반응식

HRID 1068227 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([NH:16][NH:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=2)=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].ClP(Cl)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CCN(CC)CC>CC#N.CCOC(C)=O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[N:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:18]3=[N:17][N:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 260420Triphenylphosphine dichlorideHCID 211930971-(t-Butoxycarbonyl)-4-(2-(2-pyridinyl)hydrazino)carbonyl-piperidine

생성물 1

HCID 69172981-(t-Butoxycarbonyl)-4-([1,2,4]triazolo[4,3-a]pyridin-3-yl)piperidine수율 59.5%

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 1-(t-butoxycarbonyl)-4-(2-(2-pyridinyl)hydrazino)carbonyl-piperidine (320 mg, 1.0 mmol) and dichlorotriphenylphosphorane (666 mg, 2.1 mmol) in CH3CN (10 mL) was added Et3N (0.42 mL, 3.0 mmol). After refluxing for 2h, the solution was diluted with EtOAc. The aqueous layer was extracted with EtOAc (3×). Combined organic phase was washed with brine and dried over anhydrous MgSO4. Concentration followed by flash chromatography eluting with 100% EtOAc, then 10% MeOH/CH2Cl2 afforded the title compound (180 mg) as a foamy solid. 1H NMR (500 MHz, CDCl3): δ 1.50 (s, 9H), 2.05˜2.11 (m, 4H), 3.03 (br s, 2H), 3.24 (m, 1H), 4.25 (br d, J=11.7 Hz, 1H), 6.86 (dt, J=6.9, 0.9 Hz, 1H), 7.25 (m, 1H), 7.78 (dt, J=9.4, 1.2 Hz, 1H), 7.95 (dt, J=6.8, 1.1 Hz, 1H), 7.79 (dd, J=7.3, 0.8 Hz, 1H).

후처리

  1. extractionThe aqueous layer was extracted with EtOAc (3×)
  2. washCombined organic phase was washed with brine
  3. dry with materialdried over anhydrous MgSO4
  4. concentrationConcentration
  5. washeluting with 100% EtOAc

출처 및 근거

ORD 기록
ord-fb4dd47d2c8e43a2ac9ed1451ede93c0
출처 데이터셋
uspto-grants-2001_06
특허 번호
US06248755B1

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