HCID 66931489, compound → (RS)-[5-(3-Amino-phenyl)-5-methyl-5,6-dihydro-2H-[1,4]oxazin-3-yl]-[bis-(4-methoxy-phenyl)-phenyl-methyl]-amine

HRID 1929481Notes

Reaction equation

HRID 1929481 reaction equation
COC1C=CC(C(NC2COCC(C3C=CC=C(Br)C=3)(C)N=2)(C2C=CC(OC)=CC=2)C2C=CC=CC=2)=CC=1.C(=[N:52][C:53]1[CH:54]=[C:55]([C:59]2([CH3:89])[CH2:64][O:63][CH2:62][C:61]([NH:65][C:66]([C:81]3[CH:86]=[CH:85][C:84]([O:87][CH3:88])=[CH:83][CH:82]=3)([C:73]3[CH:78]=[CH:77][C:76]([O:79][CH3:80])=[CH:75][CH:74]=3)[C:67]3[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=3)=[N:60]2)[CH:56]=[CH:57][CH:58]=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Pd]>[NH2:52][C:53]1[CH:54]=[C:55]([C:59]2([CH3:89])[CH2:64][O:63][CH2:62][C:61]([NH:65][C:66]([C:73]3[CH:74]=[CH:75][C:76]([O:79][CH3:80])=[CH:77][CH:78]=3)([C:81]3[CH:86]=[CH:85][C:84]([O:87][CH3:88])=[CH:83][CH:82]=3)[C:67]3[CH:68]=[CH:69][CH:70]=[CH:71][CH:72]=3)=[N:60]2)[CH:56]=[CH:57][CH:58]=1

Participants

4

Reactant 2

HCID 66931489HCID 66931489, compoundHCID 86651222(RS)-{5-[3-(benzhydrylidene-amino)-phenyl]-5-methyl-5,6-dihydro-2H-[1,4]oxazin-3-yl}-[bis-(4-methoxy-phenyl)-phenyl-methyl]-amine

Product 1

HCID 66931557(RS)-[5-(3-Amino-phenyl)-5-methyl-5,6-dihydro-2H-[1,4]oxazin-3-yl]-[bis-(4-methoxy-phenyl)-phenyl-methyl]-amine

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Following the general procedure described below the palladium-catalyzed amination of (RS)-[bis-(4-methoxy-phenyl)-phenyl-methyl]-[5-(3-bromo-phenyl)-5-methyl-5,6-dihydro-2H-[1,4]oxazin-3-yl]-amine followed by the hydrolysis of the intermediate (RS)-{5-[3-(benzhydrylidene-amino)-phenyl]-5-methyl-5,6-dihydro-2H-[1,4]oxazin-3-yl}-[bis-(4-methoxy-phenyl)-phenyl-methyl]-amine yielded the title compound. Mass (calculated) C32H33N3O3 [507.64]; (found) [M+H]+=508.

Sources & evidence

ORD record
ord-007d8191046a44369f4c46a38b07a5d7
Source dataset
uspto-grants-2012_05
Patent number
US08188079B2

Reaction notes

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