Lawesson's reagent → HCID 67171557, compound

HRID 1506418Notes

Reaction equation

HRID 1506418 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=O)[CH:8]([NH:14][C:15]([C:17]1[O:21][N:20]=[C:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:18]=1[C:28]([F:31])([F:30])[F:29])=O)[CH2:7][CH2:6]2.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:41])=CC=1>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9]1[S:41][C:15]([C:17]3[O:21][N:20]=[C:19]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[C:18]=3[C:28]([F:31])([F:30])[F:29])=[N:14][C:8]=1[CH2:7][CH2:6]2

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 67169548HCID 67169548, compound

Product 1

HCID 67171557HCID 67171557, compoundYield 108.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of N-(6-methoxy-1-oxo-1,2,3,4-tetrahydronaphthalen-2-yl)-3-phenyl-4-(trifluoromethyl)isoxazole-5-carboxamide (Preparation 56A, 337 mg, 0.783 mmol) and Lawesson's reagent (2,4-Bis-[4-methoxyphenyl]-1,3-dithia-2,4-diphosphetane 2,4-disulfide) (475 mg, 1.175 mmol) in THF (4.0 ml) was heated for 33 min at 140° C. on a microwave which resulted in an incomplete reaction. The reaction mixture was then microwaved for 15 min more at 140° C. The crude reaction mixture was loaded onto a 40 g silica gel Redisep® cartridge which was presaturated with 10% EtOAc-hexanes and eluted with the same. The 5-(7-methoxy-4,5-dihydronaphtho[2,1-d]thiazol-2-yl)-3-phenyl-4-(trifluoromethyl)isoxazole (0.365 g, 0.852 mmol, quant. yield) was isolated as a yellow solid. The product had an LC ret. time=2.62 min. (condition: Start % B=0; Final % B=100; Gradient Time=2 min; Flow Rate=5 ml/min; Wavelength=220; Solvent Pair=MeOH/H2O/TFA; Solvent A=0.1% TFA in MeOH: H2O (10:90); Solvent B=0.1% TFA in; MeOH: H2O (10:90); Column 1=Waters Sunfire C18 5 um 4.6×30 mm); LC/MS M+1=429.04.

Workup

  1. customresulted in an incomplete reaction
  2. customThe reaction mixture was then microwaved for 15 min more at 140° C
  3. customThe crude reaction mixture
  4. washeluted with the same

Sources & evidence

ORD record
ord-426e6aaf7eae40708a070e03404e1cb4
Source dataset
uspto-grants-2015_12
Patent number
US09216972B2

Reaction notes

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