(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 → HCID 89783528, compound

HRID 1056338Notes

Reaction equation

HRID 1056338 reaction equation
[F:1][CH2:2][C:3]([NH:6][C:7]1[N:16]([CH3:17])[C:15](=[O:18])[C:14]2[C:9](=[C:10](I)[CH:11]=[CH:12][CH:13]=2)[N:8]=1)([CH3:5])[CH3:4].[CH3:20][C@@H:21]1[C:25]2[NH:26][C:27](B3OC(C)(C)C(C)(C)O3)=[CH:28][C:24]=2[C:23](=[O:38])[NH:22]1>>[F:1][CH2:2][C:3]([NH:6][C:7]1[N:16]([CH3:17])[C:15](=[O:18])[C:14]2[C:9](=[C:10]([C:27]3[NH:26][C:25]4[C@@H:21]([CH3:20])[NH:22][C:23](=[O:38])[C:24]=4[CH:28]=3)[CH:11]=[CH:12][CH:13]=2)[N:8]=1)([CH3:5])[CH3:4]

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 897821732-((1-fluoro-2-methylpropan-2-yl)amino)-8-iodo-3-methylquinazolin-4(3H)-one

Product 1

HCID 89783528HCID 89783528, compoundYield 34%

Procedure

This compound (77 mg, 34% yield) as a brown solid was prepared according to the procedure described for Example 448, using 24(1-fluoro-2-methylpropan-2-yl)amino)-8-iodo-3-methylquinazolin-4(3H)-one (712) (221 mg, 0.59 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) (193 mg, 0.74 mmol) as the starting materials. 1H NMR (400 MHz, DMSO-d6) δ ppm 11.63 (1H, br.), 7.94 (1H, d, J=7.4 Hz), 7.80 (1H, d, J=6.8 Hz), 7.60 (1H, br.), 7.22 (1H, t, J=7.1 Hz), 6.52 (1H, s), 6.02 (1H, s), 4.74 (1H, s), 4.62 (1H, s), 4.51 (1H, m), 3.51 (3H, s), 1.45 (6H, s), 1.38 (3H, d, J=5.9 Hz). m/z (ESI, +ve) 383.9 (M+H)+.

Sources & evidence

ORD record
ord-76b363033b1d47bfb8fa98c97cfac709
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

Loading…