Potassium Carbonate → HCID 89784678, compound

HRID 1056394Notes

Reaction equation

HRID 1056394 reaction equation
C([O-])([O-])=O.[K+].[K+].[CH3:7][C@@H:8]1[C:12]2[NH:13][C:14](B3OC(C)(C)C(C)(C)O3)=[CH:15][C:11]=2[C:10](=[O:25])[NH:9]1.Br[C:27]1[CH:28]=[CH:29][CH:30]=[C:31]2[C:36]=1[N:35]=[C:34]([NH:37][C:38]([CH3:41])([CH3:40])[CH3:39])[N:33]([CH2:42][C:43]([F:46])([F:45])[F:44])[C:32]2=[O:47]>C(C1C(C(C)(C)C)=C([Pd]Cl)C=CC=1NC)(C)(C)C>[C:38]([NH:37][C:34]1[N:33]([CH2:42][C:43]([F:46])([F:44])[F:45])[C:32](=[O:47])[C:31]2[C:36](=[C:27]([C:14]3[NH:13][C:12]4[C@@H:8]([CH3:7])[NH:9][C:10](=[O:25])[C:11]=4[CH:15]=3)[CH:28]=[CH:29][CH:30]=2)[N:35]=1)([CH3:41])([CH3:39])[CH3:40]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 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 89782230HCID 89782230, compound

Product 1

HCID 89784678HCID 89784678, compoundYield 26.6%

Reagents, catalysts & solvents 1

HCID 178482226HCID 178482226, compoundCatalyst

Procedure

2-(tert-Butylamino)-8-((6R)-6-methyl-4-oxo-1,4,5,6-tetrahydropyrrolo[3,4-b]pyrrol-2-yl)-3-(2,2,2-trifluoroethyl)-4(3H)-quinazolinone (501) as a yellow solid (32 mg, 26%) was prepared according the procedures described for 408, using 1,1-bis[(di-t-butyl-p-methylaminophenyl]palladium(II) chloride (9.8 mg, 0.014 mmol, Sigma Aldrich), K2CO3 (153 mg, 1.111 mmol, Sigma Aldrich), (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 (146 mg, 0.555 mmol, 706), and 8-bromo-2-(tert-butylamino)-3-(2,2,2-trifluoroethyl)quinazolin-4(3H)-one (105 mg, 0.278 mmol, 501d). 1H NMR (400 MHz, DMSO-d6) δ ppm 11.68 (1H, s) 7.89-7.96 (1H, m) 7.83-7.88 (1H, m) 7.59 (1H, s) 7.21 (1H, t, J=7.73 Hz) 6.62 (1H, d, J=1.37 Hz) 6.28 (1H, s) 5.28 (2H, q, J=8.93 Hz) 4.50 (1H, d, J=6.26 Hz) 1.45 (9H, s) 1.36 (3H, d, J=6.65 Hz). m/z (ESI, +ve) 434.0 (M+H)+.

Sources & evidence

ORD record
ord-acdb8179b4f54385b1cc5a73632baa3e
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

Loading…