(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 89784719, compound

HRID 1056366Notes

Reaction equation

HRID 1056366 reaction equation
Br[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([NH:12][C:13]([CH3:16])([CH3:15])[CH3:14])[N:8]([CH2:17][CH3:18])[C:7]2=[O:19].[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>>[C:13]([NH:12][C:9]1[N:8]([CH2:17][CH3:18])[C:7](=[O:19])[C:6]2[C:11](=[C:2]([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:3]=[CH:4][CH:5]=2)[N:10]=1)([CH3:16])([CH3:15])[CH3:14]

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 89782161HCID 89782161, compound

Product 1

HCID 89784719HCID 89784719, compoundYield 14.5%

Procedure

This compound (8.8 mg, 11% yield) as an off-white solid was prepared according to the procedure given in 405, using 8-bromo-3-ethylquinazoline-2,4(1H,3H)-dione (52 mg, 0.160 mmol, 481d) 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 (84 mg, 0.321 mmol, 705) as the starting materials. 1H NMR (400 MHz, CDCl3) δ ppm 12.41 (1H, br. s.) 8.02 (1H, d, J=8.41 Hz) 8.06 (1H, d, J=8.61 Hz) 7.23 (1H, br. s.) 6.84 (1H, s) 5.61 (1H, br. s.) 4.66 (1H, br. s.) 4.16 (1H, d, J=7.04 Hz) 3.50 (2H, s) 1.67 (9H, s) 1.54 (3H, d, J=6.46 Hz) 1.40 (3H, t, J=6.85 Hz). m/z (ESI, +ve) 380.0 (M+H)+.

Sources & evidence

ORD record
ord-f6914c7f131c46b590fe1fe68b598662
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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