Tetrabutylammonium Fluoride → HCID 71541942, compound

HRID 1023196Notes

Reaction equation

HRID 1023196 reaction equation
[Cl:1][C:2]1[CH:28]=[CH:27][C:5]([C:6]([O:8]/[N:9]=[C:10](\[NH2:26])/[CH2:11][CH2:12][CH2:13][O:14][C:15]2[CH:16]=[C:17]3[C:22](=[CH:23][CH:24]=2)[NH:21][C:20](=[O:25])[CH2:19][CH2:18]3)=O)=[CH:4][CH:3]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>CN(C=O)C.C1COCC1>[Cl:1][C:2]1[CH:28]=[CH:27][C:5]([C:6]2[O:8][N:9]=[C:10]([CH2:11][CH2:12][CH2:13][O:14][C:15]3[CH:16]=[C:17]4[C:22](=[CH:23][CH:24]=3)[NH:21][C:20](=[O:25])[CH2:19][CH2:18]4)[N:26]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 89466729HCID 89466729, compound

Product 1

HCID 71541942HCID 71541942, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 21974620tetrahydrofuran N,N-dimethylformamideSolvent

Procedure

To a stirred solution of (Z)—N′-((4-chlorobenzoyl)oxy)-4-((2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)oxy)butanimidamide (0.030 g, 0.074 mmol) in dry DMF/THF (4 mL, 1:1) at 0° C., TBAF (1 M in THF; 0.02 mL, 0.02 mmol) was added and allowed to stir at room temperature overnight. Solvent was removed under vacuum. Ice cold water (2 mL) was added to the residue. The solid which formed was filtered and dried to yield 6-(3-(5-(4-chlorophenyl)-1,2,4-oxadiazol-3-yl)propoxy)-3,4-dihydroquinolin-2(1H)-one (0.020 g, 71%) as an off-white solid. 1H NMR: 400 MHZ, DMSO-d6: δ 2.16 (t, J=6.80 Hz, 2H), 2.39 (t, J=7.20 Hz, 2H), 2.82 (t, J=8.00 Hz, 2H), 2.95 (t, J=7.60 Hz, 2H), 4.02 (t, J=6.00 Hz, 2H), 6.71-6.78 (m, 3H), 7.72 (d, J=8.40 Hz, 2H), 8.11 (d, J=8.80 Hz, 2H), 9.89 (s, 1H). LCMS: RT 2.06 min. LCMS (ES-API), m/z 384.0 (M+H).

Workup

  1. customSolvent was removed under vacuum
  2. additionIce cold water (2 mL) was added to the residue
  3. customThe solid which formed
  4. filtrationwas filtered
  5. customdried

Sources & evidence

ORD record
ord-c90eb2c3b1314e0e8be0acab6fef59bf
Source dataset
uspto-grants-2014_05
Patent number
US08722670B2

Reaction notes

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