HCID 178418247, compound → HCID 178510298, compound

HRID 968730Notes

Reaction equation

HRID 968730 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][NH:10][C:11]2[S:12][C:13](=[CH:17][C:18]3[N:19]=[C:20]4[C:25](=[CH:26][CH:27]=3)[N:24]=[CH:23][C:22]([C:28]#[N:29])=[C:21]4OC(C)C)[C:14](=[O:16])[N:15]=2)[CH:5]=[CH:6][CH:7]=1.C(O[Na])(C)=O.O=C1C(=CC2N=C3C(=CC=2)N=CC(C#N)=C3)SC(NCC2SC=CC=2)=N1>CC(O)=O>[F:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][NH:10][C:11]2[S:12][C:13](=[CH:17][C:18]3[N:19]=[C:20]4[C:25](=[CH:26][CH:27]=3)[N:24]=[CH:23][C:22]([C:28]#[N:29])=[CH:21]4)[C:14](=[O:16])[N:15]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 178418247HCID 178418247, compoundHCID 178458711HCID 178458711, compoundHCID 178510297HCID 178510297, compound

Product 1

HCID 178510298HCID 178510298, compoundYield 30.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
120 °C

Procedure

To a mixture of 2-[2-(3-fluoro-phenyl)-ethylamino]-thiazol-4-one (40.9 mg, 0.17 mmol) (see Example 7) AcONa (160 mg, 1.95 mmol), and 6-formyl-[1,5]naphthyridine-3-carbonitrile (33.6 mg, 0.18 mmol) (see Example 11) in a sealed tube was added AcOH (0.3 mL). The reaction mixture was heated to 120° C. (oil bath) for 2 hrs. The reaction mixture was then cooled to r.t. and triturated with water. The solid was collected by filtration and washed with water, AcOEt and ether to give 6-{2-[2-(3-fluoro-phenyl)-ethylamino]-4-oxo-4H-thiazol-5-ylidenemethyl}-[1,5]naphthyridine-3-carbonitrile as a dark brown solid (20.8 mg, 30.1%). HR-ES (+) m/e calcd for C21H14FN5OS (M+H)+ 404.0976. found 404.0977.

Workup

  1. temperatureThe reaction mixture was then cooled to r.t.
  2. customtriturated with water
  3. filtrationThe solid was collected by filtration
  4. washwashed with water, AcOEt and ether

Sources & evidence

ORD record
ord-ef0a894c66584d30986102a6edce91aa
Source dataset
uspto-grants-2007_12
Patent number
US07304074B2

Reaction notes

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