4-Fluorobenzoic Acid → HCID 18146450, compound

HRID 1944527Notes

Reaction equation

HRID 1944527 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][CH:3]=1.[N:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[C:13]([NH2:21])[CH:12]=1.C(N(CC)C(C)C)(C)C>C(#N)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([NH:21][C:13]2[CH:12]=[N:11][C:20]3[C:15]([CH:14]=2)=[CH:16][CH:17]=[CH:18][CH:19]=3)=[O:8])=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 99734-Fluorobenzoic AcidHCID 113753-AminoquinolineHCID 81531Diisopropylethylamine

Product 1

HCID 18146450HCID 18146450, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 4-fluorobenzoic acid (2.57 g, 18.3 mmol), quinolin-3-ylamine (2.5 g, 17.4 mmol), O-benzotriazol-1-benzotriazol-1-yl-N,N,N′,N′-tetramethyluronium hexafluorophospate (HBTU) (7.3 g, 19.3 mmol) and N,N-diisopropylethylamine (6.4 mL, 36.7 mmol) in acetonitrile (75 mL) was stirred at ambient temperature for ten minutes, then heated at reflux for 20 hours. The solution was cooled to 0° C., and the product crystallized. The product was collected by filtration and washed with acetonitrile, to give a colorless solid, 3.86 g (79%). MS: m/z 267 (MH+). 1H NMR(DMSO-d6): δ 7.39-7.46 (m, 2 H), 7.58-7.71 (m, 2 H), 7.97-8.01 (m, 2 H), 8.11-8.16 (m, 2 H), 8.85 (d, 1 H), 9.15 (d, 1 H) and 10.73 (s, 1 H).

Workup

  1. temperatureheated
  2. temperatureat reflux for 20 hours
  3. customthe product crystallized
  4. filtrationThe product was collected by filtration
  5. washwashed with acetonitrile
  6. customto give a colorless solid, 3.86 g (79%)

Sources & evidence

ORD record
ord-1a49d313a10640db9a03a5219300abf1
Source dataset
uspto-grants-2013_03
Patent number
US08394828B2

Reaction notes

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