1H-Benzimidazol-4-ylboronic acid → HCID 68194804, compound

HRID 1631803Notes

Reaction equation

HRID 1631803 reaction equation
Cl[C:2]1[N:11]=[CH:10][C:9]2[NH:8][C:7](=[O:12])[CH:6]3[CH2:13][O:14][CH2:15][CH2:16][N:5]3[C:4]=2[N:3]=1.[NH:17]1[C:21]2[CH:22]=[CH:23][CH:24]=[C:25](B(O)O)[C:20]=2[N:19]=[CH:18]1>O1CCOCC1.C([O-])(O)=O.[Na+].C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[NH:17]1[C:21]2[CH:22]=[CH:23][CH:24]=[C:25]([C:2]3[N:11]=[CH:10][C:9]4[NH:8][C:7](=[O:12])[CH:6]5[CH2:13][O:14][CH2:15][CH2:16][N:5]5[C:4]=4[N:3]=3)[C:20]=2[N:19]=[CH:18]1

Participants

6

Reactant 2

HCID 450778561H-Benzimidazol-4-ylboronic acidHCID 866515602-chloro-6a,7,9,10-tetrahydro-[1,4]oxazino[3,4-h]pteridin-6(5H)-one

Product 1

HCID 68194804HCID 68194804, compound

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 312751,4-DioxaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

The title compound was prepared in a manner similar to EXAMPLE 84 using 2-chloro-6a,7,9,10-tetrahydro-[1,4]oxazino[3,4-h]pteridin-6(5H)-one (PREPARATION x1, 50 mg, 0.208 mmol), 1H-benzo[d]imidazol-4-ylboronic acid (71.5 mg, 0.441 mmol), and PdCl2(dppf) (7.60 mg, 10.39 μmol) in dioxane (2 mL) and aqueous saturated NaHCO3 (0.4 mL). 1H NMR (400 MHz, DMSO-d6) δ 3.10-3.19 (m, 1H), 3.50-3.59 (m, 2H), 3.99 (d, J=3.28 Hz, 1H), 4.18 (dd, J=11.24, 3.66 Hz, 1H), 4.43 (dd, J=10.61, 3.79 Hz, 1H), 4.59-4.71 (m, 1H), 7.49-7.67 (m, 1H), 7.90 (d, J=8.08 Hz, 1H), 8.03 (s, 1H), 8.39 (d, J=7.83 Hz, 1H), 9.23 (br s, 1H), 11.03 (s, 1H). ESI-MS m/z [M+H]+ calc'd for C16H14N6O2, 323.12. found 323.2.

Sources & evidence

ORD record
ord-83a1a2d620dd47f88f3281a5fb61daa7
Source dataset
uspto-grants-2014_07
Patent number
US08791107B2

Reaction notes

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