(+-)-1-Aminoindan → HCID 178433108, compound

HRID 1393954Notes

Reaction equation

HRID 1393954 reaction equation
I.[CH3:2][CH:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]=[C:5](SC)[NH:4]1.[NH2:15][CH:16]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH2:18][CH2:17]1>C(#N)C.C(O)(C(F)(F)F)=O>[CH:16]1([NH:15][C:5]2[NH:4][CH:3]([CH3:2])[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[N:6]=2)[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH2:18][CH2:17]1

Participants

5

Reactant 2

HCID 123445(+-)-1-AminoindanHCID 178503334HCID 178503334, compound

Product 1

HCID 178433108HCID 178433108, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolvent2×HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
85 °C

Procedure

4-Methyl-2-methylsulfanyl-3,4-dihydro-quinazoline hydroiodide (31 mg, 0.10 mmol) and (+/−)-1-aminoindane (17 mg, 0.12 mmol) were suspended in acetonitrile (1 ml) and heated in a screw-capped vial to 85° C. (12 h). The product was isolated from the reaction mixture by preparative HPLC (YMC CombiPrep C18 column 50×20 mm, solvent gradient 5-95% CH3CN in 0.1% TFA(aq) over 7.0 min, λ=230 nm, flow rate 40 ml/min) to give the title compound (MS: m/e=264.2 [M+H+]).

Sources & evidence

ORD record
ord-e63a4ada6595411ab54dd2276b54583d
Source dataset
uspto-grants-2008_03
Patent number
US07348332B2

Reaction notes

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