4-Fluorophenylacetyl chloride → HCID 136338546, compound

HRID 1158637Notes

Reaction equation

HRID 1158637 reaction equation
[OH:1][N:2]=[C:3]([C:5]1[C:14]([OH:15])=[C:13]2[C:8]([CH:9]=[CH:10][CH:11]=[N:12]2)=[CH:7][N:6]=1)[NH2:4].[F:16][C:17]1[CH:22]=[CH:21][C:20]([CH2:23][C:24]([Cl:26])=O)=[CH:19][CH:18]=1>O1CCOCC1>[ClH:26].[F:16][C:17]1[CH:22]=[CH:21][C:20]([CH2:23][C:24]2[O:1][N:2]=[C:3]([C:5]3[C:14]([OH:15])=[C:13]4[C:8]([CH:9]=[CH:10][CH:11]=[N:12]4)=[CH:7][N:6]=3)[N:4]=2)=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 37449884-Fluorophenylacetyl chlorideHCID 136395587HCID 136395587, compound

Product 1

HCID 136338546HCID 136338546, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
160 °C

Procedure

To a suspension of N′,8-dihydroxy[1,6]naphthyridine-7-carboximidamide (50 mg, 0.244 mmol) in dioxane (3 mL) was-added 4-fluorophenylacetyl chloride (40 μL, 0.293 mmol). The reaction vessel was sealed and heated at 160° C. in a microwave chamber for 10 minutes. The solids were collected on a filter, then triturated with methano/ether to provide 7-[5-(4-fluorobenzyl)-1,2,4-oxadiazol-3-yl][1,6]naphthyridin-8-ol hydrochloride (13 mg, 15%) as an orange solid. 1H NMR (CD3OD) δ 9.43 (d, J=4 Hz, 1H), 9.34 (s, 1H), 9.05 (d, J=8.0 Hz, 1H), 8.14 (dd, J=8.4, 4.8 Hz, 1H), 7.48 (dd, J=8.4, 5.2 Hz, 2H), 7.12 (t, J=8.8 Hz, 2H), 4.92 (s, 2 H); MS m/z 323 (M+1).

Workup

  1. customThe reaction vessel was sealed
  2. customThe solids were collected on a filter
  3. customtriturated with methano/ether

Sources & evidence

ORD record
ord-0618d309d83a4800b22f6e2cbcf131c3
Source dataset
uspto-grants-2010_10
Patent number
US07812016B2

Reaction notes

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