3-Methyl-1-[4-(tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]urea → 1-(4-(5-(2-Chloro-4-(methylsulfonyl)benzyl)-5,6,6a,7,9,10-hexahydro-[1,4]oxazino[3,4-h]pteridin-2-yl)phenyl)-3-methylurea

HRID 1631768Notes

Reaction equation

HRID 1631768 reaction equation
Cl[C:2]1[N:11]=[CH:10][C:9]2[N:8]([CH2:12][C:13]3[CH:18]=[CH:17][C:16]([S:19]([CH3:22])(=[O:21])=[O:20])=[CH:15][C:14]=3[Cl:23])[CH2:7][CH:6]3[CH2:24][O:25][CH2:26][CH2:27][N:5]3[C:4]=2[N:3]=1.[CH3:28][NH:29][C:30]([NH:32][C:33]1[CH:38]=[CH:37][C:36](B2OC(C)(C)C(C)(C)O2)=[CH:35][CH:34]=1)=[O:31]>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]>[Cl:23][C:14]1[CH:15]=[C:16]([S:19]([CH3:22])(=[O:20])=[O:21])[CH:17]=[CH:18][C:13]=1[CH2:12][N:8]1[CH2:7][CH:6]2[CH2:24][O:25][CH2:26][CH2:27][N:5]2[C:4]2[N:3]=[C:2]([C:36]3[CH:35]=[CH:34][C:33]([NH:32][C:30]([NH:29][CH3:28])=[O:31])=[CH:38][CH:37]=3)[N:11]=[CH:10][C:9]1=2

Participants

6

Reactant 2

HCID 177502733-Methyl-1-[4-(tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ureaHCID 866700902-Chloro-5-(2-chloro-4-(methylsulfonyl)benzyl)-5,6,6a,7,9,10-hexahydro-[1,4]oxazino[3,4-h]pteridine

Product 1

HCID 601977621-(4-(5-(2-Chloro-4-(methylsulfonyl)benzyl)-5,6,6a,7,9,10-hexahydro-[1,4]oxazino[3,4-h]pteridin-2-yl)phenyl)-3-methylurea

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 5 using 2-chloro-5-(2-chloro-4-(methylsulfonyl)benzyl)-5,6,6a,7,9,10-hexahydro-[1,4]oxazino[3,4-h]pteridine (PREPARATION x6, 175 mg, 0.408 mmol), (1-methyl-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)urea (225 mg, 0.815 mmol) and PdCl2(dppf) (14.91 mg, 0.020 mmol) in dioxane (5 mL) and aqueous saturated NaHCO3 (1 mL). 1H NMR (400 MHz, DMSO-d6) δ 2.61-2.71 (m, 3H), 3.28-3.31 (m, 2H), 3.53-3.66 (m, 1H), 3.87-4.02 (m, 2H), 4.03-4.15 (m, 1H), 4.59-4.79 (m, 2H), 4.79-4.91 (m, 1H), 6.14-6.25 (m, 1H), 7.32-7.38 (m, 1H), 7.53-7.62 (m, 2H), 7.63-7.71 (m, 1H), 7.81-7.90 (m, 1H), 7.99-8.12 (m, 3H), 8.91-9.05 (m, 1H). ESI-MS m/z [M+H]+ calc'd for C25H27ClN6O4S, 543.15. found 543.5.

Sources & evidence

ORD record
ord-e502a98048ca41069157c4339fed5dcf
Source dataset
uspto-grants-2014_07
Patent number
US08791107B2

Reaction notes

Loading…