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Tetrahydrofuran → 6-[5-(1-Amino-cyclopropyl)-pyridin-3-yl]-1-methyl-3,4-dihydro-1H-quinolin-2-one

HRID 1774814
Notes
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Reaction equation

HRID 1774814 reaction equation
[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]3[CH:13]=[C:14]([C:18]4(C(O)=O)[CH2:20][CH2:19]4)[CH:15]=[N:16][CH:17]=3)=[CH:9][CH:10]=2)[CH2:5][CH2:4][C:3]1=[O:24].C1(P([N:39]=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.C1COCC1>C1(C)C=CC=CC=1>[NH2:39][C:18]1([C:14]2[CH:13]=[C:12]([C:8]3[CH:7]=[C:6]4[C:11](=[CH:10][CH:9]=3)[N:2]([CH3:1])[C:3](=[O:24])[CH2:4][CH2:5]4)[CH:17]=[N:16][CH:15]=2)[CH2:20][CH2:19]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 199401P,P-Diphenylphosphinic azideHCID 86679167HCID 86679167, compound

Product 1

HCID 715336316-[5-(1-Amino-cyclopropyl)-pyridin-3-yl]-1-methyl-3,4-dihydro-1H-quinolin-2-oneYield 74.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

To solution of 1-(5-(1-methyl-2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)pyridin-3-yl)cyclopropanecarboxylic acid (0.551 g, 1.52 mmol) in toluene (20 mL) were added TEA (0.185 g, 1.83 mmol) and diphenylphosphoryl azide (0.419 g, 1.52 mmol) and then the reaction mixture was heated to reflux for 4 h. After cooling to 0° C., a 1 M solution of sodium trimethylsilanoate in THF (3.04 mL, 3.04 mmol) was added and the mixture was stirred for 45 min at room temperature. After quenching with 0.1 M aq. HCl (40 mL), the aqueous solution was washed with ether (2 times), then basified with 1 M aq. NaOH and then extracted with DCM (2×100 mL). The combined organics were washed with brine, dried over Na2SO4, filtered and evaporated to dryness to give the title compound (0.333 g, 71%) as a yellow foam. MS: 294.4 (M+H+).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 4 h
  3. customAfter quenching with 0.1 M aq. HCl (40 mL)
  4. washthe aqueous solution was washed with ether (2 times)
  5. extractionextracted with DCM (2×100 mL)
  6. washThe combined organics were washed with brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. customevaporated to dryness

Sources & evidence

ORD record
ord-ef25db3aead842bd8b39c2deb7fd9506
Source dataset
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09260408B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes