HCID 178418247, compound → HCID 178458600, compound

HRID 968745Notes

Reaction equation

HRID 968745 reaction equation
[Cl:1][C:2]1[CH:28]=[C:27]([F:29])[CH:26]=[CH:25][C:3]=1[CH2:4][NH:5][C:6]1[S:7][C:8](=[CH:12][C:13]2[N:14]=[C:15]3[C:20](=[CH:21][CH:22]=2)[N:19]=[CH:18][C:17](C#N)=[CH:16]3)[C:9](=[O:11])[N:10]=1.C(O[Na])(C)=O.[CH:35]([O:38]C1C=CN=C2C=1N=C(C=C1SC(NC3CC3C3C=CC=CC=3)=NC1=O)C=C2)([CH3:37])[CH3:36]>CC(O)=O>[Cl:1][C:2]1[CH:28]=[C:27]([F:29])[CH:26]=[CH:25][C:3]=1[CH2:4][NH:5][C:6]1[S:7][C:8](=[CH:12][C:13]2[CH:22]=[CH:21][C:20]3[C:15](=[C:16]([O:38][CH:35]([CH3:37])[CH3:36])[CH:17]=[CH:18][N:19]=3)[N:14]=2)[C:9](=[O:11])[N:10]=1

Participants

5

Reactant 3

HCID 178418247HCID 178418247, compoundHCID 178458598HCID 178458598, compoundHCID 178510295HCID 178510295, compound

Product 1

HCID 178458600HCID 178458600, compoundYield 59.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

To a mixture of 2-(2-chloro-4-fluoro-benzylamino)-thiazol-4-one (41.4 mg, 0.16 mmol) (see Example 18), AcONa (160 mg, 1.95 mmol), and 8-isopropoxy-[1,5]naphthyridine-2-carbaldehyde (38.9 mg, 0.18 mmol) (see Example 20) in a sealed tube was added AcOH(0.3 mL). The reaction mixture was heated to 100° 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, acetone and ether to give 2-(2-chloro-4-fluoro-benzylamino)-5-(8-isopropoxy-[1,5]naphthyridin-2-ylmethylene)-thiazol-4-one as a light brown solid (43.5 mg, 59.5%). HR-ES (+) m/e calcd for C22H18FClN4O2S (M+H)+ 457.0896. found 457.0897.

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-ba81743b57454a6eac214e6748289ae0
Source dataset
uspto-grants-2007_12
Patent number
US07304074B2

Reaction notes

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