(R)-(-)-1-Aminoindan → HCID 178419898, compound

HRID 1393952Notes

Reaction equation

HRID 1393952 reaction equation
I.CS[C:4]1[NH:13][CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=1.[NH2:14][C@H:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH2:17][CH2:16]1>C(#N)C.C(O)(C(F)(F)F)=O>[N:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH2:12][NH:13][C:4]=1[NH:14][C@H:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH2:17][CH2:16]1

Participants

5

Reactant 2

HCID 2733933(R)-(-)-1-AminoindanHCID 178503336HCID 178503336, compound

Product 1

HCID 178419898HCID 178419898, compoundYield 24.4%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolvent2×HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
85 °C

Procedure

2-Methylsulfanyl-3,4-dihydro-quinazoline hydroiodide (50 mg, 0.28 mmol) and (R)-1-aminoindane (37 mg, 0.28 mmol) were suspended in acetonitrile (1 ml) and heated in a screw-capped vial to 85° C. (6 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 6.0 min, λ=230 nm, flow rate 40 ml/min) to give the title compound (18 mg, 24%).

Sources & evidence

ORD record
ord-04f515d0a3a54cceafe0cf856247bcfa
Source dataset
uspto-grants-2008_03
Patent number
US07348332B2

Reaction notes

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