1-(5-(3-(Aminomethyl)phenyl)-3,4-dihydroquinolin-1(2H)-yl)-4-(2,3-dimethylphenoxy)butan-1-one → N-(2-Aminoethyl)-3-((4-(1-(4-(2,3-dimethylphenoxy)butanoyl)-1,2,3,4-tetrahydroquinolin-5-yl)-1H-pyrazol-1-yl)methyl)benzamide

HRID 2175277Notes

Reaction equation

HRID 2175277 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:119]([CH3:120])=[CH:118][CH:117]=[CH:116][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[CH:92]=[N:93][N:94]([CH2:96][C:97]4[CH:98]=[C:99]([CH:113]=[CH:114][CH:115]=4)[C:100]([NH:102][CH2:103][CH2:104][NH:105]C(=O)OC(C)(C)C)=[O:101])[CH:95]=3)[CH:87]=[CH:88][CH:89]=2)[CH2:84][CH2:83][CH2:82]1)=[O:80]>>[NH2:105][CH2:104][CH2:103][NH:102][C:100](=[O:101])[C:99]1[CH:113]=[CH:114][CH:115]=[C:97]([CH2:96][N:94]2[CH:95]=[C:91]([C:86]3[CH:87]=[CH:88][CH:89]=[C:90]4[C:85]=3[CH2:84][CH2:83][CH2:82][N:81]4[C:79](=[O:80])[CH2:78][CH2:77][CH2:76][O:75][C:74]3[CH:116]=[CH:117][CH:118]=[C:119]([CH3:120])[C:73]=3[CH3:72])[CH:92]=[N:93]2)[CH:98]=1

Participants

4

Reactant 3

HCID 709819111-(5-(3-(Aminomethyl)phenyl)-3,4-dihydroquinolin-1(2H)-yl)-4-(2,3-dimethylphenoxy)butan-1-oneHCID 70982891tert-Butyl 3-(1-(4-(2,3-dimethylphenoxy)butanoyl)-1,2,3,4-tetrahydroquinolin-5-yl)benzylcarbamateHCID 86712593tert-Butyl 2-(3-((4-(1-(4-(2,3-dimethylphenoxy)butanoyl)-1,2,3,4-tetrahydroquinolin-5-yl)-1H-pyrazol-1-yl)methyl)benzamido)ethylcarbamate

Product 1

HCID 70983323N-(2-Aminoethyl)-3-((4-(1-(4-(2,3-dimethylphenoxy)butanoyl)-1,2,3,4-tetrahydroquinolin-5-yl)-1H-pyrazol-1-yl)methyl)benzamide

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 2-(3-((4-(1-(4-(2,3-dimethylphenoxy)butanoyl)-1,2,3,4-tetrahydroquinolin-5-yl)-1H-pyrazol-1-yl)methyl)benzamido)ethylcarbamate. LCMS, [M+H]+=566.3. 1H NMR (400 MHz, MeOD) δ 7.89-7.73 (m, 2H), 7.65 (s, 1H), 7.56-7.40 (m, 3H), 7.32-7.19 (m, 2H), 7.17 (br. s, 1H), 6.96 (t, J=7.9 Hz, 1H), 6.71-6.59 (m, 2H), 5.43 (s, 2H), 3.86 (br. s, 2H), 3.74 (t, J=6.8 Hz, 2H), 3.50 (t, J=6.3 Hz, 2H), 2.90 (t, J=6.3 Hz, 2H), 2.81 (t, J=6.8 Hz, 2H), 2.48 (br. s, 2H), 2.12 (dt, J=12.4, 6.3 Hz, 2H), 2.03 (s, 3H), 1.85-1.75 (m, 2H), 1.74 (s, 3H).

Sources & evidence

ORD record
ord-3f0dab8faaa246d7b4803470b377da48
Source dataset
uspto-grants-2015_06
Patent number
US09062028B2

Reaction notes

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