HCID 178418247, compound → HCID 178510296, compound

HRID 968733Notes

Reaction equation

HRID 968733 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][C:15]=1[F:16])[CH2:5][NH:6][C:7]1[S:8][CH2:9][C:10](=[O:12])[N:11]=1.C(O[Na])(C)=O.O=C1C(=[CH:28][C:29]2[N:30]=[C:31]3[C:36](=[CH:37][CH:38]=2)[N:35]=[CH:34][C:33]([C:39]#[N:40])=[CH:32]3)SC(NCC2SC=CC=2)=N1>CC(O)=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][C:15]=1[F:16])[CH2:5][NH:6][C:7]1[S:8][C:9](=[CH:28][C:29]2[N:30]=[C:31]3[C:36](=[CH:37][CH:38]=2)[N:35]=[CH:34][C:33]([C:39]#[N:40])=[CH:32]3)[C:10](=[O:12])[N:11]=1

Participants

5

Reactant 3

HCID 178418247HCID 178418247, compoundHCID 178510297HCID 178510297, compoundHCID 178516941HCID 178516941, compound

Product 1

HCID 178510296HCID 178510296, compoundYield 45.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
120 °C

Procedure

To a mixture of 2-(3-chloro-4-fluoro-benzylamino)-thiazol-4-one (41.4 mg, 0.16 mmol) (prepared as described below) 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 3 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-(3-chloro-4-fluoro-benzylamino)-4-oxo-4H-thiazol-5-ylidenemethyl]-[1,5]naphthyridine-3-carbonitrile as a light brown solid (30.6 mg, 45.1%). HR-ES (+) m/e calcd for C20H11FClN5OS (M+H)+ 424.0430. found 424.0431.

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-72531deee3564b4c8e28ef1ce1d2bbc0
Source dataset
uspto-grants-2007_12
Patent number
US07304074B2

Reaction notes

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