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

HRID 1056359Notes

Reaction equation

HRID 1056359 reaction equation
[C:1]([NH:5][C:6]1[N:15]([CH2:16][CH2:17][O:18][CH2:19][CH2:20][O:21][CH3:22])[C:14](=[O:23])[C:13]2[C:8](=[C:9](I)[CH:10]=[CH:11][CH:12]=2)[N:7]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:25][C@@H:26]1[C:30]2[NH:31][C:32](B3OC(C)(C)C(C)(C)O3)=[CH:33][C:29]=2[C:28](=[O:43])[NH:27]1>>[C:1]([NH:5][C:6]1[N:15]([CH2:16][CH2:17][O:18][CH2:19][CH2:20][O:21][CH3:22])[C:14](=[O:23])[C:13]2[C:8](=[C:9]([C:32]3[NH:31][C:30]4[C@@H:26]([CH3:25])[NH:27][C:28](=[O:43])[C:29]=4[CH:33]=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 897820042-(tert-butylamino)-8-iodo-3-(2-(2-methoxy-ethoxy)ethyl)quinazolin-4(3H)-one

Product 1

HCID 897841632-(tert-butylamino)-3-(2-(2-methoxyethoxyl)ethyl)-8-((6R)-6-methyl-4-oxo-1,4,5,6-tetrahydropyrrolo[3,4-b]pyrrol-2-yl)-4(3H)-quinazolinoneYield 40.2%

Procedure

This compound (102 mg, 40% yield) as a tan amorphous solid was prepared according to the procedure described for Example 448, using 2-(tert-butylamino)-8-iodo-3-(2-(2-methoxyethoxyl)ethyl)quinazolin-4(3H)-one (716) (250 mg, 0.56 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) (178 mg, 0.68 mmol) as the starting materials. 1H NMR (400 MHz, MeOH-d4) δ ppm 7.99 (2H, dd, J=7.6, 1.8 Hz), 7.23 (1H, t, J=7.7 Hz), 6.75 (1H, s), 4.69 (1H, q, J=6.8 Hz), 4.27-4.38 (2H, m), 3.90 (2H, t, J=4.3 Hz), 3.67-3.74 (2H, m), 3.55-3.63 (2H, m), 1.60 (9H, s), 1.52 (3H, d, J=6.8 Hz), 1.22 (6H, s). m/z (ESI, +ve) 454.0 (M+H)+.

Sources & evidence

ORD record
ord-3f98cbc2286c4f3b91b106008bff2039
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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