HCID 89781918, compound → HCID 89783472, compound

HRID 1056334Notes

Reaction equation

HRID 1056334 reaction equation
I[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([O:12][C:13]1([CH3:16])[CH2:15][CH2:14]1)[N:8]([CH3:17])[C:7]2=[O:18].[CH3:19][C@@H:20]1[C:24]2[NH:25][C:26](B3OC(C)(C)C(C)(C)O3)=[CH:27][C:23]=2[C:22](=[O:37])[NH:21]1>>[CH3:17][N:8]1[C:7](=[O:18])[C:6]2[C:11](=[C:2]([C:26]3[NH:25][C:24]4[C@@H:20]([CH3:19])[NH:21][C:22](=[O:37])[C:23]=4[CH:27]=3)[CH:3]=[CH:4][CH:5]=2)[N:10]=[C:9]1[O:12][C:13]1([CH3:16])[CH2:15][CH2:14]1

Participants

3

Reactant 2

HCID 89781918HCID 89781918, compoundHCID 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)-one

Product 1

HCID 89783472HCID 89783472, compoundYield 31%

Procedure

This compound (66 mg, 31% yield) as a brown solid was prepared according to the procedure described for Example 448, using 8-iodo-3-methyl-2-(1-methylcyclopropoxy)quinazolin-4(3H)-one (717) (210 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) (201 mg, 0.76 mmol) as the starting materials. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.21 (1H, br.), 8.18 (1H, d, J=7.8 Hz), 7.94 (1H, d, J=7.6 Hz), 7.74 (1H, s), 7.41 (1H, t, J=7.7 Hz), 7.16 (1H, s), 4.65 (1H, d, J=6.5 Hz), 3.36 (3H, S), 1.78 (3H, s), 1.39 (3H, d, J=6.5 Hz), 1.25 (2H, m), 0.94 (2H, m). m/z (ESI, +ve) 365.0 (M+H)+.

Sources & evidence

ORD record
ord-0f9fbc46b2d74966b878f5899f90edf9
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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