8-bromo-N-tert-butyl-N-methylquinazolin-2-amine → 2-(2-(tert-butyl(methyl)amino)quinazolin-8-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one

HRID 1056258Notes

Reaction equation

HRID 1056258 reaction equation
CC1(C)C(C)(C)OB([C:9]2[NH:17][C:16]3[CH2:15][CH2:14][NH:13][C:12](=[O:18])[C:11]=3[CH:10]=2)O1.Br[C:21]1[CH:22]=[CH:23][CH:24]=[C:25]2[C:30]=1[N:29]=[C:28]([N:31]([C:33]([CH3:36])([CH3:35])[CH3:34])[CH3:32])[N:27]=[CH:26]2>>[C:33]([N:31]([CH3:32])[C:28]1[N:27]=[CH:26][C:25]2[C:30](=[C:21]([C:9]3[NH:17][C:16]4[CH2:15][CH2:14][NH:13][C:12](=[O:18])[C:11]=4[CH:10]=3)[CH:22]=[CH:23][CH:24]=2)[N:29]=1)([CH3:36])([CH3:35])[CH3:34]

Participants

3

Reactant 2

HCID 897820998-bromo-N-tert-butyl-N-methylquinazolin-2-amineHCID 897834962-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-YL)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-C]pyridin-4-one

Product 1

HCID 897832612-(2-(tert-butyl(methyl)amino)quinazolin-8-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-oneYield 22.9%

Procedure

2-(2-(tert-butyl(methyl)amino)quinazolin-8-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (8 mg, 22% yield) as a yellow crystalline solid was prepared according to the procedure described for Example 370, using 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (609) (146 mg, 0.56 mmol), and 8-bromo-N-(tert-butyl)-N-methylquinazolin-2-amine (377a) (30 mg, 0.10 mmol) as the starting materials. 1H NMR (400 MHz, CDCl3) δ ppm 12.87 (1H, br. s.), 9.04 (1H, s), 8.07 (1H, dd, J=7.5, 1.3 Hz), 7.52 (1H, dd, J=7.8, 1.2 Hz), 7.23-7.30 (1H, m), 7.11 (1H, d, J=2.0 Hz), 5.40 (1H, br. s.), 3.66 (2H, td, J=6.8, 2.5 Hz), 3.37 (3H, s), 2.98 (2H, t, J=6.8 Hz), 1.67 (9H, s). m/z (ESI, +ve ion) 350.1 (M+H)+.

Sources & evidence

ORD record
ord-616d42b7634d4e31abc947d010b20275
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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