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Triphenylphosphine → tert-Butyl (2S)-3-(2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-yloxy)-2-ethylpentylcarbamate

HRID 2035563
Notes
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Reaction equation

HRID 2035563 reaction equation
[N:1]1[N:2]=[C:3]([C:10]2[CH:19]=[CH:18][C:17]3[C:12](=[C:13]([OH:20])[CH:14]=[CH:15][CH:16]=3)[N:11]=2)[N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12.[CH2:21]([C@H:23]([CH:33](O)[CH2:34][CH3:35])[CH2:24][NH:25][C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29])[CH3:22].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1.O.C(OCC)(=O)C>[N:1]1[N:2]=[C:3]([C:10]2[CH:19]=[CH:18][C:17]3[C:12](=[C:13]([O:20][CH:33]([CH2:34][CH3:35])[C@@H:23]([CH2:21][CH3:22])[CH2:24][NH:25][C:26](=[O:32])[O:27][C:28]([CH3:29])([CH3:30])[CH3:31])[CH:14]=[CH:15][CH:16]=3)[N:11]=2)[N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 86654358Tert-butyl (2s)-2-ethyl-3-hydroxypentylcarbamateHCID 136337804HCID 136337804, compound

Product 1

HCID 86654357tert-Butyl (2S)-3-(2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-yloxy)-2-ethylpentylcarbamate

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-([1,2,4]Triazolo[4,3-a]pyridin-3-yl)quinolin-8-ol (101 mg, 0.385 mmol), tert-butyl (2S )-2-ethyl-3-hydroxypentylcarbamate (89 mg, 0.385 mmol), PPh3 (151 mg, 0.577 mmol) and DEAD (90.9 μL, 0.577 mmol) were combined at ambient temperature in 5 mL anhydrous THF. The reaction mixture was heated at reflux for 6 hours. The crude mixture was cooled to ambient temperature and diluted with water and ethyl acetate. The crude mixture was extracted with ethyl acetate, and the combined organic layers were dried over Na2SO4 and concentrated in vacuo to provide the desired product.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 6 hours
  3. extractionThe crude mixture was extracted with ethyl acetate
  4. dry with materialthe combined organic layers were dried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-99a4b523910d44b1b9438f1424b2ff83
Source dataset
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08575145B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes