1H-1,2,4-Triazole → HCID 44555546, compound

HRID 885049Notes

Reaction equation

HRID 885049 reaction equation
Br[C:2]1[N:3]=[CH:4][C:5]([O:31][CH3:32])=[C:6]2[C:10]([C:11](=[O:30])[C:12]([N:14]3[CH2:23][CH2:22][C:21]4[C:16](=[CH:17][CH:18]=[CH:19][C:20]=4[C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=4)[CH2:15]3)=[O:13])=[CH:9][NH:8][C:7]=12.[NH:33]1[CH:37]=[N:36][CH:35]=[N:34]1>N1C=CC=CC=1.[Cu]>[CH3:32][O:31][C:5]1[CH:4]=[N:3][C:2]([N:33]2[CH:37]=[N:36][CH:35]=[N:34]2)=[C:7]2[NH:8][CH:9]=[C:10]([C:11](=[O:30])[C:12]([N:14]3[CH2:23][CH2:22][C:21]4[C:16](=[CH:17][CH:18]=[CH:19][C:20]=4[C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=4)[CH2:15]3)=[O:13])[C:6]=12

Participants

5

Reactant 2

HCID 92571H-1,2,4-TriazoleHCID 580260391-(7-bromo-4-methoxy-1H-pyrrolo[2,3-c]pyridin-3-yl)-2-(5-(pyridin-2-yl)-3,4-dihydroisoquinolin-2(1H)-yl)ethane-1,2-dione

Product 1

HCID 44555546HCID 44555546, compound

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 1049PyridineSolvent

Conditions

Temperature
145 °C

Procedure

A mixture of 1-(7-bromo-4-methoxy-1H-pyrrolo[2,3-c]pyridin-3-yl)-2-(5-(pyridin-2-yl)-3,4-dihydroisoquinolin-2(1H)-yl)ethane-1,2-dione (80 mg, 0.163 mmol), 1H-1,2,4-triazole (45.0 mg, 0.651 mmol) and copper (20.69 mg, 0.326 mmol) in pyridine (1 mL) was heated at 145° C. for 10 hours, LCMS indicated the formation of desired product. The reaction mixture was filtered and the clear solution purified by prep. HPLC to give 1-(4-methoxy-7-(1H-1,2,4-triazol-1-yl)-1H-pyrrolo[2,3-c]pyridin-3-yl)-2-(5-(pyridin-2-yl)-3,4-dihydroisoquinolin-2(1H)-yl)ethane-1,2-dione as pale yellow solid (28 mg, 35%). LCMS: m/e 480.11 (M+H)+, 1.52 min (method 9). 1H NMR (500 MHz, MeOD) δ ppm 2.81-3.10 (m, 2H) 3.70-4.04 (m, 5H) 4.76-5.10 (m, 2H) 7.37-7.72 (m, 3H) 7.80-7.93 (m, 1H) 8.00-8.22 (m, 2H) 8.30-8.42 (m, 2H) 8.55-8.75 (m, 1H) 8.83-8.99 (m, 1H) 9.39 (s, 1H).

Sources & evidence

ORD record
ord-77ed8cdab65242328c81084d689a4ba8
Source dataset
uspto-grants-2012_08
Patent number
US08242124B2

Reaction notes

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