(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 89783643, compound

HRID 1056360Notes

Reaction equation

HRID 1056360 reaction equation
[C:1]([NH:5][C:6]1[N:15]([CH:16]2[CH2:18][CH2:17]2)[C:14](=[O:19])[C:13]2[C:8](=[C:9](I)[CH:10]=[CH:11][CH:12]=2)[N:7]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:21][C@@H:22]1[C:26]2[NH:27][C:28](B3OC(C)(C)C(C)(C)O3)=[CH:29][C:25]=2[C:24](=[O:39])[NH:23]1>>[C:1]([NH:5][C:6]1[N:15]([CH:16]2[CH2:18][CH2:17]2)[C:14](=[O:19])[C:13]2[C:8](=[C:9]([C:28]3[NH:27][C:26]4[C@@H:22]([CH3:21])[NH:23][C:24](=[O:39])[C:25]=4[CH:29]=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 89782169HCID 89782169, compound

Product 1

HCID 89783643HCID 89783643, compoundYield 58.3%

Procedure

This compound (73 mg, 57% yield) as a tan amorphous solid was prepared according to the procedure described for Example 448, using 2-(tert-butylamino)-3-cyclopropyl-8-iodoquinazolin-4(3H)-one (718) (125 mg, 0.32 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) (85 mg, 0.32 mmol) as the starting materials. 1H NMR (400 MHz, DMSO-d6) δ ppm 11.99 (1H, br. s.), 7.89 (1H, d, J=7.4 Hz), 7.85 (1H, d, J=7.8 Hz), 7.65 (1H, s), 7.16 (1H, t, J=7.7 Hz), 6.74 (1H, s), 6.15 (1H, s), 4.48-4.59 (1H, m), 2.88 (1H, br. s.), 1.54 (9H, s), 1.38 (3H, d, J=6.5 Hz), 1.27 (2H, d, J=6.7 Hz), 0.78 (2H, br. s.). m/z (ESI, +ve) 392.0 (M+H)+.

Sources & evidence

ORD record
ord-9657aa2bf46e4404a1d7265363d041ad
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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