(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 89793956, compound

HRID 1056339Notes

Reaction equation

HRID 1056339 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([CH3:17])[CH2:16][CH2:15][CH2:14]1)[N:8]([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>>[CH3:18][N:8]1[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]=[C:9]1[NH:12][C:13]1([CH3:17])[CH2:16][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 897821268-iodo-3-methyl-2-((1-methylcyclobutyl)amino)quinazolin-4(3H)-one

Product 1

HCID 89793956HCID 89793956, compoundYield 54.6%

Procedure

This compound (169 mg, 54% yield) as a brown solid was prepared according to the procedure described for Example 448, using 8-iodo-3-methyl-2-((1-methylcyclobutyl)amino)quinazolin-4(3H)-one (711) (303 mg, 0.82 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) (215 mg, 0.82 mmol) as the starting materials. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.27 (1H, br.), 8.00 (1H, dd, J=7.6, 1.4 Hz), 7.85 (1H, dd, J=7.8, 1.4 Hz), 7.66 (1H, s), 7.15 (1H, t, J=7.7 Hz), 6.98 (1H, s), 6.81 (1H, s), 4.60 (1H, q, J=6.5 Hz), 3.41 (3H, s), 2.38 (2H, m), 2.14 (2H, m), 1.88 (2H, m), 1.67 (3H, s), 1.40 (3H, d, J=6.7 Hz). m/z (ESI, +ve) 378.2 (M+H)+.

Sources & evidence

ORD record
ord-9655e7a8bac8476ebf1356e631a52b54
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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