Triethylamine → HCID 22051083, compound

HRID 1867028Notes

Reaction equation

HRID 1867028 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][N:5]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([F:15])[CH:10]=2)[C:4](=[O:16])[CH:3]=1.C(N(CC)CC)C.[F:24][C:25]1[CH:33]=[CH:32][C:28]([C:29](Cl)=[O:30])=[CH:27][CH:26]=1>C(#N)C.CN(C1C=CN=CC=1)C>[F:24][C:25]1[CH:33]=[CH:32][C:28]([C:29]([NH:1][C:2]2[CH:7]=[CH:6][N:5]([CH2:8][C:9]3[CH:14]=[CH:13][CH:12]=[C:11]([F:15])[CH:10]=3)[C:4](=[O:16])[CH:3]=2)=[O:30])=[CH:27][CH:26]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 678794-Fluorobenzoyl chlorideHCID 22051076HCID 22051076, compound

Product 1

HCID 22051083HCID 22051083, compoundYield 79.8%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 4-amino-1-(3-fluorobenzyl)pyridin-2(1H)-one (0.263 g, 1.2 mmol) in acetonitrile (7 mL) was added a DMAP (ca.), triethylamine (0.25 mL, 1.8 mmol) and 4-fluorobenzoyl chloride (0.213 mL, 1.8 mmol). The reaction mixture stirred at 0° C. for 25 minutes and then filtered. The solid was washed with 10% citric acid and water to afford the desired compound (0.326 g, 79%) after drying. 1H-NMR (d6DMSO, 400 MHz) δ 7.98 (m, 2H), 7.71 (d, 1H, J=7.6 Hz), 7.35 (m, 3H), 7.08 (m, 3H), 6.98 (d, 1H, J=2.4 Hz), 6.61 (dd, 1H, J=2.4 Hz, 2.4 Hz), 5.03 (s, 2H); ESLRMS m/z 341.1.

Workup

  1. filtrationfiltered
  2. washThe solid was washed with 10% citric acid and water

Sources & evidence

ORD record
ord-c81db1806eae44b2be52e38cb775b05d
Source dataset
uspto-grants-2009_12
Patent number
US07629363B2

Reaction notes

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