(2,4-Dimethoxypyrimidin-5-yl)boronic acid → 6-(4-Chloro-phenyl)-2-(2,4-dimethoxy-pyrimidin-5-yl)-5-(1,3-dimethyl-1H-pyrazol-4-yl)-1-isopropyl-5,6-dihydro-1H-pyrrolo[3,4-b]pyrrol-4-one

HRID 2204401Notes

Reaction equation

HRID 2204401 reaction equation
Br[C:2]1[N:6]([CH:7]([CH3:9])[CH3:8])[C:5]2[CH:10]([C:21]3[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=3)[N:11]([C:14]3[C:15]([CH3:20])=[N:16][N:17]([CH3:19])[CH:18]=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>>[Cl:27][C:24]1[CH:25]=[CH:26][C:21]([CH:10]2[C:5]3[N:6]([CH:7]([CH3:9])[CH3:8])[C:2]([C:33]4[C:34]([O:36][CH3:37])=[N:35][C:30]([O:29][CH3:28])=[N:31][CH:32]=4)=[CH:3][C:4]=3[C:12](=[O:13])[N:11]2[C:14]2[C:15]([CH3:20])=[N:16][N:17]([CH3:19])[CH:18]=2)=[CH:22][CH:23]=1

Participants

5

Reactant 4

HCID 2736209(2,4-Dimethoxypyrimidin-5-yl)boronic acidHCID 23005336(5-Cyano-2-Methoxyphenyl)Boronic AcidHCID 867031482-Bromo-6-(4-chloro-phenyl)-5-(1,3-dimethyl-1H-pyrazol-4-yl)-1-isopropyl-5,6-dihydro-1H-pyrrolo[3,4-b]pyrrol-4-oneHCID 867031692-bromo-5-(5-chloro-2-methyl-phenyl)-6-(4-chloro-phenyl)-1-isopropyl-5,6-dihydro-1H-pyrrolo[3,4-b]pyrrol-4-one

Product 1

HCID 867032136-(4-Chloro-phenyl)-2-(2,4-dimethoxy-pyrimidin-5-yl)-5-(1,3-dimethyl-1H-pyrazol-4-yl)-1-isopropyl-5,6-dihydro-1H-pyrrolo[3,4-b]pyrrol-4-one

Procedure

The title compound was prepared in analogy to the procedure described for Example 17 but 2-bromo-6-(4-chloro-phenyl)-5-(1,3-dimethyl-1H-pyrazol-4-yl)-1-isopropyl-5,6-dihydro-1H-pyrrolo[3,4-b]pyrrol-4-one (Intermediate AY) 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: 1.06 min (HPLC 3); ESI-MS: tR=1.01 min, [M+H]+ 507/509 (LC-MS 1); TLC: Rf=0.22 (9:1 CH2Cl2/MeOH).

Workup

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

Sources & evidence

ORD record
ord-cab73dfa81eb44dc96ee581d0bc70513
Source dataset
uspto-grants-2016_06
Patent number
US09365576B2

Reaction notes

Loading…