(R)-6-methyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyrrolo[3,4-b]pyrrol-4(1H)-one → 2-(tert-butylamino)-3-(2-methoxyethyl)-8-((6R)-6-methyl-4-oxo-1,4,5,6-tetrahydropyrrolo[3,4-b]pyrrol-2-yl)-4(3H)-quinazolinone

HRID 1056333Notes

Reaction equation

HRID 1056333 reaction equation
[C:1]([NH:5][C:6]1[N:15]([CH2:16][CH2:17][O:18][CH3:19])[C:14](=[O:20])[C:13]2[C:8](=[C:9](I)[CH:10]=[CH:11][CH:12]=2)[N:7]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:22][C@@H:23]1[C:27]2[NH:28][C:29](B3OC(C)(C)C(C)(C)O3)=[CH:30][C:26]=2[C:25](=[O:40])[NH:24]1>>[C:1]([NH:5][C:6]1[N:15]([CH2:16][CH2:17][O:18][CH3:19])[C:14](=[O:20])[C:13]2[C:8](=[C:9]([C:29]3[NH:28][C:27]4[C@@H:23]([CH3:22])[NH:24][C:25](=[O:40])[C:26]=4[CH:30]=3)[CH:10]=[CH:11][CH:12]=2)[N:7]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 89781988(R)-6-methyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyrrolo[3,4-b]pyrrol-4(1H)-oneHCID 897820952-(tert-butylamino)-8-iodo-3-(2-methoxyethyl)quinazolin-4(3H)-one

Product 1

HCID 897840062-(tert-butylamino)-3-(2-methoxyethyl)-8-((6R)-6-methyl-4-oxo-1,4,5,6-tetrahydropyrrolo[3,4-b]pyrrol-2-yl)-4(3H)-quinazolinoneYield 39%

Procedure

This compound (97 mg, 39% yield) as a brown solid was prepared according to the procedure described for Example 448, using 2-(tert-butylamino)-8-iodo-3-(2-methoxyethyl)quinazolin-4(3H)-one (715) (245 mg, 0.61 mmol) and (R)-6-methyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyrrolo[3,4-b]pyrrol-4(1H)-one (705) (208 mg, 0.79 mmol) as the starting materials. 1H NMR (400 MHz, DMSO-d6) δ ppm 11.95 (1H, br.), 7.90 (2H, m), 7.66 (1H, s), 7.20 (1H, t, J=7.7 Hz), 6.74 (1H, s), 6.51 (1H, s), 4.55 (1H, q, J=6.7 Hz), 4.28 (2H, m), 3.71 (2H, t, J=4.5 Hz), 3.36 (3H, s), 1.49 (9H, s), 1.38 (3H, d, J=6.7 Hz). m/z (ESI, +ve) 410.0 (M+H)+.

Sources & evidence

ORD record
ord-0cf7ba710a614f0c8dcf542e53dac21a
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

Loading…