(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 → 3-methyl-2-((1-methylcyclopropyl)amino)-8-((6R)-6-methyl-4-oxo-1,4,5,6-tetrahydropyrrolo[3,4-b]pyrrol-2-yl)-4(3H)-quinazolinone

HRID 1056327Notes

Reaction equation

HRID 1056327 reaction equation
I[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([NH:12][C:13]1([CH3:16])[CH2:15][CH2:14]1)[N:8]([CH3:17])[C:7]2=[O:18].[CH3:19][C@@H:20]1[C:24]2[NH:25][C:26](B3OC(C)(C)C(C)(C)O3)=[CH:27][C:23]=2[C:22](=[O:37])[NH:21]1>>[CH3:17][N:8]1[C:7](=[O:18])[C:6]2[C:11](=[C:2]([C:26]3[NH:25][C:24]4[C@@H:20]([CH3:19])[NH:21][C:22](=[O:37])[C:23]=4[CH:27]=3)[CH:3]=[CH:4][CH:5]=2)[N:10]=[C:9]1[NH:12][C:13]1([CH3:16])[CH2:15][CH2:14]1

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 897821798-iodo-3-methyl-2-((1-methylcyclopropyl)amino)quinazolin-4(3H)-one

Product 1

HCID 897838013-methyl-2-((1-methylcyclopropyl)amino)-8-((6R)-6-methyl-4-oxo-1,4,5,6-tetrahydropyrrolo[3,4-b]pyrrol-2-yl)-4(3H)-quinazolinoneYield 52%

Procedure

This compound (85 mg, 52% yield) as a brown solid was prepared according to the procedure described for Example 448, using 8-iodo-3-methyl-2-((1-methylcyclopropyl)amino)quinazolin-4(3H)-one (713) (160 mg, 0.45 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) (130 mg, 0.50 mmol) as the starting materials. 1H NMR (400 MHz, DMSO-d6) δ ppm 13.02 (1H, br.), 8.13 (1H, dd, J=7.6, 1.4 Hz), 7.83 (1H, dd, J=7.8, 1.4 Hz), 7.69 (2H, d, J=3.1 Hz), 7.18 (1H, t, J=7.7 Hz), 6.96 (1H, s), 4.64 (1H, q, J=6.6 Hz), 3.40 (3H, s), 1.56 (3H, s), 1.37 (3H, d, J=6.7 Hz), 1.01 (2H, m), 0.86 (2H, m). MS (ESI, pos. ion) m/z: 364.0 (M+1).

Sources & evidence

ORD record
ord-82036d2bdfdd424881a76452c9a4a303
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

Loading…