1-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)cyclopentanecarbonitrile → 1-(4-(5-Amino-6-(1-oxo-1,2,3,4-tetrahydroisoquinolin-6-yl)pyrazin-2-yl)phenyl)cyclopentanecarbonitrile

HRID 2091567Notes

Reaction equation

HRID 2091567 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:14]=[CH:13][C:12]([C:15]3([C:20]#[N:21])[CH2:19][CH2:18][CH2:17][CH2:16]3)=[CH:11][CH:10]=2)O1.[NH2:23][C:24]1[C:25]([C:31]2[CH:32]=[C:33]3[C:38](=[CH:39][CH:40]=2)[C:37](=[O:41])[NH:36][CH2:35][CH2:34]3)=[N:26][C:27](Br)=[CH:28][N:29]=1>>[NH2:23][C:24]1[N:29]=[CH:28][C:27]([C:9]2[CH:10]=[CH:11][C:12]([C:15]3([C:20]#[N:21])[CH2:16][CH2:17][CH2:18][CH2:19]3)=[CH:13][CH:14]=2)=[N:26][C:25]=1[C:31]1[CH:32]=[C:33]2[C:38](=[CH:39][CH:40]=1)[C:37](=[O:41])[NH:36][CH2:35][CH2:34]2

Participants

3

Reactant 2

HCID 706550061-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)cyclopentanecarbonitrileHCID 866702106-(3-amino-6-bromopyrazin-2-yl)-3,4-dihydroisoquinolin-1(2H)-one

Product 1

HCID 706547561-(4-(5-Amino-6-(1-oxo-1,2,3,4-tetrahydroisoquinolin-6-yl)pyrazin-2-yl)phenyl)cyclopentanecarbonitrileYield 44%

Procedure

General method A was applied to 1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)cyclopentanecarbonitrile (149 mg, 0.5 mmol) and 6-(3-amino-6-bromopyrazin-2-yl)-3,4-dihydroisoquinolin-1(2H)-one (180 mg, 0.5 mmol) to give 1-(4-(5-amino-6-(1-oxo-1,2,3,4-tetrahydroisoquinolin-6-yl)pyrazin-2-yl)phenyl)cyclopentanecarbonitrile as a yellow solid (89 mg, 0.22 mmol, 44% yield) after purification by preparatory reverse phase HPLC. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.60 (s, 1H), 8.02 (d, J=8.3 Hz, 3H), 7.96 (d, J=8.0 Hz, 1H), 7.72-7.78 (m, 1H), 7.70 (s, 1H), 7.57 (m, J=8.5 Hz, 3H), 3.38-3.45 (m, 2H), 2.99 (t, J=6.4 Hz, 2H), 2.37-2.46 (m, 2H), 2.03-2.16 (m, 2H), 1.84-1.94 (m, 4H); MS (EI) m/z=410.5 [M+1]+.

Sources & evidence

ORD record
ord-ede55a4492904a0e84cb82fa0d85f5a4
Source dataset
uspto-grants-2013_05
Patent number
US08440652B2

Reaction notes

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