HCID 178418247, compound → HCID 178458603, compound

HRID 968741Notes

Reaction equation

HRID 968741 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#N)=[C:21]4[O:30][CH:31]([CH3:33])[CH3:32])[C:14](=[O:16])[N:15]=2)[CH:5]=[CH:6][CH:7]=1.C(O[Na])(C)=O.C(OC1C=CN=C2C=1N=C(C=C1SC(NC3CC3C3C=CC=CC=3)=NC1=O)C=C2)(C)C>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[CH:27]=[CH:26][C:25]4[C:20](=[C:21]([O:30][CH:31]([CH3:33])[CH3:32])[CH:22]=[CH:23][N:24]=4)[N:19]=3)[C:14](=[O:16])[N:15]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 178418247HCID 178418247, compoundHCID 178458598HCID 178458598, compoundHCID 178458711HCID 178458711, compound

Product 1

HCID 178458603HCID 178458603, compoundYield 65.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

To a mixture of 2-[2-(3-fluoro-phenyl)-ethylamino]-thiazol-4-one (38.1 mg, 0.16 mmol) (see Example 7), 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 4 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-(3-fluoro-phenyl)-ethylamino]-5-(8-isopropoxy-[1,5]naphthyridin-2-ylmethylene)-thiazol-4-one as a light green solid (45.9 mg, 65.8%). HR-ES (+) m/e calcd for C23H21FN4O2S (M+H)+ 437.1442. found 437.1443.

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-f8fdfb2269dd46038b11e11908c3a6ec
Source dataset
uspto-grants-2007_12
Patent number
US07304074B2

Reaction notes

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