1-(5-Bromo-3,4-dihydroquinolin-1(2H)-yl)-4-(2,3-dimethylphenoxy)butan-1-one → 1-(5-(1-(3-Aminobenzyl)-1H-pyrazol-4-yl)-3,4-dihydroquinolin-1(2H)-yl)-4-(2,3-dimethylphenoxy)butan-1-one

HRID 2175258Notes

Reaction equation

HRID 2175258 reaction equation
NC[C:3]1[CH:4]=[C:5]([CH:36]=[CH:37][CH:38]=1)[CH2:6][N:7]1[CH:11]=[C:10]([C:12]2[CH:21]=[CH:20][CH:19]=[C:18]3[C:13]=2[CH2:14][CH2:15][CH2:16][N:17]3[C:22](=[O:35])[CH2:23][CH2:24][CH2:25][O:26][C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([CH3:33])[C:28]=2[CH3:34])[CH:9]=[N:8]1.BrC1C=[N:42]N(CC2C=C(C=CC=2)CNC(=O)OC(C)(C)C)C=1.BrC1C=CC=C2C=1CCCN2C(=O)CCCOC1C=CC=C(C)C=1C.CC1C(C)=CC=CC=1OCCCC(N1C2C(=C(B3OC(C)(C)C(C)(C)O3)C=CC=2)CCC1)=O.CC1(C)C(C)(C)OB(C2C=NN(CC3C=C(NC(=O)OC(C)(C)C)C=CC=3)C=2)O1>>[NH2:42][C:3]1[CH:4]=[C:5]([CH:36]=[CH:37][CH:38]=1)[CH2:6][N:7]1[CH:11]=[C:10]([C:12]2[CH:21]=[CH:20][CH:19]=[C:18]3[C:13]=2[CH2:14][CH2:15][CH2:16][N:17]3[C:22](=[O:35])[CH2:23][CH2:24][CH2:25][O:26][C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([CH3:33])[C:28]=2[CH3:34])[CH:9]=[N:8]1

Participants

6

Reactant 5

HCID 709817961-(5-Bromo-3,4-dihydroquinolin-1(2H)-yl)-4-(2,3-dimethylphenoxy)butan-1-oneHCID 709820304-(2,3-dimethylphenoxy)-1-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydroquinolin-1(2H)-yl)butan-1-oneHCID 709825821-(5-(1-(3-(Aminomethyl)benzyl)-1H-pyrazol-4-yl)-3,4-dihydroquinolin-1(2H)-yl)-4-(2,3-dimethylphenoxy)butan-1-oneHCID 70982704tert-Butyl 3-((4-bromo-1H-pyrazol-1-yl)methyl)benzylcarbamateHCID 70983056tert-Butyl 3-((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)methyl)phenylcarbamate

Product 1

HCID 867125851-(5-(1-(3-Aminobenzyl)-1H-pyrazol-4-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-(1-(3-(aminomethyl)benzyl)-1H-pyrazol-4-yl)-3,4-dihydroquinolin-1(2H)-yl)-4-(2,3-dimethylphenoxy)butan-1-one except that tert-butyl 3-((4-bromo-1H-pyrazol-1-yl)methyl)benzylcarbamate was replaced by 1-(5-bromo-3,4-dihydroquinolin-1(2H)-yl)-4-(2,3-dimethylphenoxy)butan-1-one and 4-(2,3-dimethylphenoxy)-1-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydroquinolin-1(2H)-yl)butan-1-one was replaced by tert-butyl 3-((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)methyl)phenylcarbamate. LCMS, [M+H]+=495.4.

Sources & evidence

ORD record
ord-97a88699de534335b7859c3d5a5a62ab
Source dataset
uspto-grants-2015_06
Patent number
US09062028B2

Reaction notes

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