Iodoacetonitrile → HCID 86612794, compound

HRID 2364503Notes

Reaction equation

HRID 2364503 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]2[CH:18]=[C:17]3[C:12]([C:13]([OH:25])=[C:14]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:15](=[O:19])[NH:16]3)=[N:11][CH:10]=2)=[CH:4][CH:3]=1.I[CH2:27][C:28]#[N:29]>O1CCCC1>[C:28]([CH2:27][N:16]1[C:17]2[C:12](=[N:11][CH:10]=[C:9]([CH2:8][C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)[CH:18]=2)[C:13]([OH:25])=[C:14]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:15]1=[O:19])#[N:29]

Participants

4

Reactant 2

HCID 69356IodoacetonitrileHCID 54729997Ethyl 7-[(4-Fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate

Product 1

HCID 86612794HCID 86612794, compoundYield 101.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a similar manner to that described in example 316 step 1, from ethyl 7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate (29 mg, 0.085 mmol) lithium (bis-trimethylsilyl)amide (0.17 mL of a 1 M solution in tetrahydrofuran) and iodoacetonitrile (0.04 mL, 0.51 mmol) was prepared ethyl 1-(cyanomethyl)-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate (33 mg, 95% yield) as a yellow oil. Product was carried on without further purification. 1H NMR (CDCl3) δ 8.51 (s, 1 H), 7.40 (s, 1 H), 7.15-7.09 (m, 2 H), 7.01-6.96 (m, 2 H), 5.10 (s, 2 H), 4.46 (m, 2 H), 4.13 (s, 2 H), 1.41 (m, 3 H); MS m/z 404 (M+23).

Sources & evidence

ORD record
ord-207ca53477f5424a8870e97914fe3bf0
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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