2-(2-Methoxyphenoxy)ethyl amine → HCID 178489623, compound

HRID 505322Notes

Reaction equation

HRID 505322 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][CH:10]=[CH:9][C:4]=1[O:5][CH2:6][CH2:7][NH2:8].I.CS[C:16]1[NH:25][CH2:24][C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[N:17]=1>C(#N)C.C(O)(C(F)(F)F)=O>[N:17]1[C:18]2[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:24][NH:25][C:16]=1[NH:8][CH2:7][CH2:6][O:5][C:4]1[CH:9]=[CH:10][CH:11]=[CH:12][C:3]=1[O:2][CH3:1]

Participants

5

Reactant 2

HCID 17130052-(2-Methoxyphenoxy)ethyl amineHCID 178503336HCID 178503336, compound

Product 1

HCID 178489623HCID 178489623, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolvent2×HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
80 °C

Procedure

2-(2-Methoxy-phenoxy)-ethylamine (42 mg, 0.25 mmol) was added to a solution of 2-methylsulfanyl-3,4-dihydro-quinazoline hydroiodide (70 mg, 0.23 mmol) in acetonitrile (1 ml), and the mixture was heated overnight (80° C.) in a screw-capped vial. The title compound (42 mg, 62%) was then isolated from the reaction mixture by preparative, reverse-phase HPLC (YMC CombiPrep C18 column 50×20 mm, solvent gradient 5-95% CH3CN in 0.1% TFA(aq) over 6.0 min, λ=230 nm, flow rate 40 ml/min).

Sources & evidence

ORD record
ord-e4015751a29a46ceaf9aeea1adb07db4
Source dataset
uspto-grants-2010_08
Patent number
US07781441B2

Reaction notes

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