(2,4-Dimethoxypyrimidin-5-yl)boronic acid → HCID 178494056, compound

HRID 2204399Notes

Reaction equation

HRID 2204399 reaction equation
Br[C:2]1[N:6]([CH:7]([CH3:9])[CH3:8])[C:5]2[CH:10]([C:21]3[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[CH:23][CH:22]=3)[N:11]([C@H:14]3[CH2:19][CH2:18][C@H:17]([OH:20])[CH2:16][CH2:15]3)[C:12](=[O:13])[C:4]=2[CH:3]=1.[CH3:29][O:30][C:31]1[N:36]=[C:35]([O:37][CH3:38])[C:34](B(O)O)=[CH:33][N:32]=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>>[CH3:29][O:30][C:31]1[N:36]=[C:35]([O:37][CH3:38])[C:34]([C:2]2[N:6]([CH:7]([CH3:9])[CH3:8])[C:5]3[CH:10]([C:21]4[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[CH:23][CH:22]=4)[N:11]([C@H:14]4[CH2:19][CH2:18][C@H:17]([OH:20])[CH2:16][CH2:15]4)[C:12](=[O:13])[C:4]=3[CH:3]=2)=[CH:33][N:32]=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 178456155HCID 178456155, compound

Product 1

HCID 178494056HCID 178494056, compound

Procedure

The title compound was prepared in analogy to the procedure described for Example 17 but 4-[2-bromo-5-(trans-4-hydroxy-cyclohexyl)-1-isopropyl-4-oxo-1,4,5,6-tetrahydro-pyrrolo[3,4-b]pyrrol-6-yl]-benzonitrile (Intermediate AV) 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: 5.54 min (HPLC 2); ESI-MS: tR=0.86 min, [M+H]+ 502 (LC-MS 1); TLC: Rf=0.11 (EtOAc).

Workup

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

Sources & evidence

ORD record
ord-61c8fa60e3c34e8595546ea5a06a1f59
Source dataset
uspto-grants-2016_06
Patent number
US09365576B2

Reaction notes

Loading…