(2,4-Dimethoxypyrimidin-5-yl)boronic acid → HCID 86703209, compound

HRID 2204398Notes

Reaction equation

HRID 2204398 reaction equation
Br[C:2]1[N:6]([CH:7]([CH3:9])[CH3:8])[C:5]2[CH:10]([C:20]3[CH:27]=[CH:26][C:23]([C:24]#[N:25])=[CH:22][CH:21]=3)[N:11]([CH:14]3[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)[C:12](=[O:13])[C:4]=2[CH:3]=1.[CH3:28][O:29][C:30]1[N:35]=[C:34]([O:36][CH3:37])[C:33](B(O)O)=[CH:32][N:31]=1.BrC1N(C(C)C)C2C(C3C=CC(Cl)=CC=3)N(C3C=C(Cl)C=CC=3C)C(=O)C=2C=1.C(C1C=CC(OC)=C(B(O)O)C=1)#N>>[CH3:28][O:29][C:30]1[N:35]=[C:34]([O:36][CH3:37])[C:33]([C:2]2[N:6]([CH:7]([CH3:8])[CH3:9])[C:5]3[CH:10]([C:20]4[CH:21]=[CH:22][C:23]([C:24]#[N:25])=[CH:26][CH:27]=4)[N:11]([CH:14]4[CH2:15][CH2:16][O:17][CH2:18][CH2:19]4)[C:12](=[O:13])[C:4]=3[CH:3]=2)=[CH:32][N:31]=1

Participants

5

Reactant 4

HCID 2736209(2,4-Dimethoxypyrimidin-5-yl)boronic acidHCID 23005336(5-Cyano-2-Methoxyphenyl)Boronic AcidHCID 867031692-bromo-5-(5-chloro-2-methyl-phenyl)-6-(4-chloro-phenyl)-1-isopropyl-5,6-dihydro-1H-pyrrolo[3,4-b]pyrrol-4-oneHCID 86703210HCID 86703210, compound

Product 1

HCID 86703209HCID 86703209, compound

Procedure

The title compound was prepared in analogy to the procedure described for Example 17 but 4-[2-bromo-1-isopropyl-4-oxo-5-(tetrahydro-pyran-4-yl)-1,4,5,6-tetrahydro-pyrrolo[3,4-b]pyrrol-6-yl]-benzonitrile (Intermediate AU) and 2,4-dimethoxypyrimidine-5-boronic acid were used instead of 2-bromo-5-(5-chloro-2-methyl-phenyl)-6-(4-chloro-phenyl)-1-isopropyl-5,6-dihydro-1H-pyrrolo[3,4-b]pyrrol-4-one and 5-cyano-2-methoxyphenylboronic acid respectively. The title compound was obtained as a white solid. tR: 0.98 min (HPLC 3); ESI-MS: tR=0.92 min, [M+H]+ 488 (LC-MS 1); TLC: Rf=0.20 (EtOAc).

Workup

  1. customThe title compound was prepared in analogy to the procedure

Sources & evidence

ORD record
ord-480dd7f623ae47dfac2df7ceda72be96
Source dataset
uspto-grants-2016_06
Patent number
US09365576B2

Reaction notes

Loading…