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

HRID 1068227ノート

反応式

HRID 1068227 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-fb4dd47d2c8e43a2ac9ed1451ede93c0
出典データセット
uspto-grants-2001_06
特許番号
US06248755B1

反応ノート

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