HCID 178418247, compound → HCID 178510291, compound

HRID 968727Notes

Reaction equation

HRID 968727 reaction equation
C(O[C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([CH:15]=[C:16]3[S:20][C:19]([NH:21][CH:22]4[CH2:24][CH:23]4[C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)=[N:18][C:17]3=[O:31])[N:13]=2)[N:8]=[CH:7][C:6]=1[C:32]#[N:33])(C)C.C(O[Na])(C)=O.O=C1C(=CC2N=C3C(=CC=2)N=CC(C#N)=C3)SC(NCC2SC=CC=2)=N1>CC(O)=O>[O:31]=[C:17]1[C:16](=[CH:15][C:12]2[N:13]=[C:14]3[C:9](=[CH:10][CH:11]=2)[N:8]=[CH:7][C:6]([C:32]#[N:33])=[CH:5]3)[S:20][C:19]([NH:21][CH:22]2[CH2:24][CH:23]2[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[N:18]1

Participants

5

Reactant 3

HCID 178418247HCID 178418247, compoundHCID 178458707HCID 178458707, compoundHCID 178510297HCID 178510297, compound

Product 1

HCID 178510291HCID 178510291, compoundYield 21.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

To a mixture of 2-(trans)-phenylcyclopylamino-thiazol-4-one (38.0 mg, 0.16 mmol) (see Example 3), AcONa (160 mg, 1.95 mmol), and 6-formyl-[1,5]naphthyridine-3-carbonitrile (38.5 mg, 0.21 mmol) (see Example 11), in a sealed tube was added AcOH (0.3 mL). The reaction mixture was heated to 100° C. (oil bath) for 5 hrs. The reaction mixture was then cooled to r.t. and triturated with water. The solid was collected by filtration and washed with water acetone and ether to give 6-[4-oxo-2-(2-phenyl-cyclopropylamino)-4H-thiazol-5-ylidenemethyl]-[1,5]naphthyridine-3-carbonitrile as a yellowish solid (13.7 mg, 18.3%). HR-ES (+) m/e calcd for C22H15N5OS (M+H)+ 398.1070. found 398.1071.

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 acetone and ether

Sources & evidence

ORD record
ord-891a2a24a8ba4ebbb77373ae20b30341
Source dataset
uspto-grants-2007_12
Patent number
US07304074B2

Reaction notes

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