Triethylamine → HCID 86699720, compound

HRID 1844111Notes

Reaction equation

HRID 1844111 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][C:5](=[O:11])[NH:6]2.[F:12][C:13]1[CH:18]=[CH:17][C:16]([N:19]2[CH:24]=[CH:23][CH:22]=[C:21]([C:25](O)=[O:26])[C:20]2=[O:28])=[CH:15][CH:14]=1.F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.C(N(CC)CC)C>C(#N)C.CN(C=O)C>[F:12][C:13]1[CH:18]=[CH:17][C:16]([N:19]2[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([NH:1][C:2]3[CH:10]=[CH:9][CH:8]=[C:7]4[C:3]=3[CH2:4][C:5](=[O:11])[NH:6]4)=[O:26])[C:20]2=[O:28])=[CH:15][CH:14]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 122374724-Aminoindolin-2-oneHCID 210815271-(4-Fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxylic acid

Product 1

HCID 86699720HCID 86699720, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

4-aminooxindole (80 mg, 0.54 mmol) was made to react to 1-(4-fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxylic acid (125.5 mg, 0.54 mmol) in the presence of O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate (TBTU, 250 mg, 0.78 mmol) and triethylamine (TEA, 0.23 mL, 1.62 mmol) in a mixture of dry DMF and acetonitrile (1:3, 6 mL) under rt for 14 hours. Resultant solid was collected by filter, washed by methanol, water and ether, and dried to give 1-(4-fluorophenyl)-2-oxo-N-(2-oxoindolin-4-yl)-1,2-dihydropyridine-3-carboxamide: YD: 56%; mp: 293-295° C. 1H-NMR (400 MHz, DMSO-d6): 11.77 (s, 1H), 10.41 (s, 1H), 8.58 (dd, J=7.6, 2 Hz, 1H), 8.10 (dd, J=6.6, 2 Hz, 1H), 7.77 (d, J=8.4 Hz, 1H), 7.59 (m, 2H), 7.41 (d, J=8.8 Hz, 2H), 7.17 (dd, J=8, 7.6 Hz, 1H), 6.71 (dd, 7.6, 6.6 Hz, 1H), 6.68 (d, J=7.6 Hz, 1H), 3.36 (s, 2H). (C20H14N3O3F. 0.3; H2O) C, H, N.

Workup

  1. customResultant solid was collected
  2. filtrationby filter
  3. washwashed by methanol, water and ether
  4. customdried

Sources & evidence

ORD record
ord-5681bdcdbd3e4ce2a04f6bb958883d97
Source dataset
uspto-grants-2015_02
Patent number
US08946282B2

Reaction notes

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