1-(5-(3-(Aminomethyl)phenyl)-3,4-dihydroquinolin-1(2H)-yl)-4-(2,3-dimethylphenoxy)butan-1-one → 1-(5-(2-(3-Aminobenzyl)-2H-tetrazol-5-yl)-3,4-dihydroquinolin-1(2H)-yl)-4-(2,3-dimethylphenoxy)butan-1-one

HRID 2175268Notes

Reaction equation

HRID 2175268 reaction equation
NCC1C=C(C2C=CC=C3C=2CCCN3C(=O)CCCOC2C=CC=C(C)C=2C)C=CC=1.CC1C(C)=CC=CC=1OCCCC(N1C2C(=C(C3C=C(C=CC=3)CNC(=O)OC(C)(C)C)C=CC=2)CCC1)=O.[CH3:72][C:73]1[C:114]([CH3:115])=[CH:113][CH:112]=[CH:111][C:74]=1[O:75][CH2:76][CH2:77][CH2:78][C:79]([N:81]1[C:90]2[C:85](=[C:86]([C:91]3[N:92]=[N:93][N:94]([CH2:96][C:97]4[CH:98]=[C:99]([NH:103]C(=O)OC(C)(C)C)[CH:100]=[CH:101][CH:102]=4)[N:95]=3)[CH:87]=[CH:88][CH:89]=2)[CH2:84][CH2:83][CH2:82]1)=[O:80]>>[NH2:103][C:99]1[CH:98]=[C:97]([CH:102]=[CH:101][CH:100]=1)[CH2:96][N:94]1[N:93]=[N:92][C:91]([C:86]2[CH:87]=[CH:88][CH:89]=[C:90]3[C:85]=2[CH2:84][CH2:83][CH2:82][N:81]3[C:79](=[O:80])[CH2:78][CH2:77][CH2:76][O:75][C:74]2[CH:111]=[CH:112][CH:113]=[C:114]([CH3:115])[C:73]=2[CH3:72])=[N:95]1

Participants

4

Reactant 3

HCID 709819111-(5-(3-(Aminomethyl)phenyl)-3,4-dihydroquinolin-1(2H)-yl)-4-(2,3-dimethylphenoxy)butan-1-oneHCID 70982618tert-Butyl 3-((5-(1-(4-(2,3-dimethylphenoxy)butanoyl)-1,2,3,4-tetrahydroquinolin-5-yl)-2H-tetrazol-2-yl)methyl)phenylcarbamateHCID 70982891tert-Butyl 3-(1-(4-(2,3-dimethylphenoxy)butanoyl)-1,2,3,4-tetrahydroquinolin-5-yl)benzylcarbamate

Product 1

HCID 867125891-(5-(2-(3-Aminobenzyl)-2H-tetrazol-5-yl)-3,4-dihydroquinolin-1(2H)-yl)-4-(2,3-dimethylphenoxy)butan-1-one

Procedure

The title compound was prepared using a procedure analogous to 1-(5-(3-(aminomethyl)phenyl)-3,4-dihydroquinolin-1(2H)-yl)-4-(2,3-dimethylphenoxy)butan-1-one except that tert-butyl 3-(1-(4-(2,3-dimethylphenoxy)butanoyl)-1,2,3,4-tetrahydroquinolin-5-yl)benzylcarbamate was replaced with tert-butyl 3-((5-(1-(4-(2,3-dimethylphenoxy)butanoyl)-1,2,3,4-tetrahydroquinolin-5-yl)-2H-tetrazol-2-yl)methyl)phenylcarbamate. LCMS, [M+H]+=497.3.

Sources & evidence

ORD record
ord-18dc51f753f04aff8d843f8e4b8c6867
Source dataset
uspto-grants-2015_06
Patent number
US09062028B2

Reaction notes

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