(2,4-Dimethoxypyrimidin-5-yl)boronic acid → 5-(5-Chloro-1-methyl-6-oxo-1,6-dihydro-pyridin-3-yl)-6-(4-chloro-phenyl)-2-(2,4-dimethoxy-pyrimidin-5-yl)-1-isopropyl-4-oxo-1,4,5,6-tetrahydro-pyrrolo[3,4-b]pyrrole-3-carboxylic acid ethyl ester

HRID 2204417Notes

Reaction equation

HRID 2204417 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]2[C:17](=[O:18])[N:16]([C:19]3[CH:24]=[C:23]([Cl:25])[C:22](=[O:26])[N:21]([CH3:27])[CH:20]=3)[CH:15]([C:28]3[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=3)[C:8]=2[N:9]([CH:12]([CH3:14])[CH3:13])[C:10]=1Br)=[O:5])[CH3:2].[CH3:35][O:36][C:37]1[N:42]=[C:41]([O:43][CH3:44])[C:40](B(O)O)=[CH:39][N:38]=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>>[CH2:1]([O:3][C:4]([C:6]1[C:7]2[C:17](=[O:18])[N:16]([C:19]3[CH:24]=[C:23]([Cl:25])[C:22](=[O:26])[N:21]([CH3:27])[CH:20]=3)[CH:15]([C:28]3[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=3)[C:8]=2[N:9]([CH:12]([CH3:14])[CH3:13])[C:10]=1[C:40]1[C:41]([O:43][CH3:44])=[N:42][C:37]([O:36][CH3:35])=[N:38][CH:39]=1)=[O:5])[CH3:2]

Participants

5

Reactant 4

HCID 2736209(2,4-Dimethoxypyrimidin-5-yl)boronic acidHCID 23005336(5-Cyano-2-Methoxyphenyl)Boronic AcidHCID 867031622-Bromo-5-(5-chloro-1-methyl-6-oxo-1,6-dihydro-pyridin-3-yl)-6-(4-chloro-phenyl)-1-isopropyl-4-oxo-1,4,5,6-tetrahydro-pyrrolo[3,4-b]pyrrole-3-carboxylic acid ethyl esterHCID 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 867032385-(5-Chloro-1-methyl-6-oxo-1,6-dihydro-pyridin-3-yl)-6-(4-chloro-phenyl)-2-(2,4-dimethoxy-pyrimidin-5-yl)-1-isopropyl-4-oxo-1,4,5,6-tetrahydro-pyrrolo[3,4-b]pyrrole-3-carboxylic acid ethyl ester

Procedure

The title compound was prepared in analogy to the procedure described for Example 17 but 2-bromo-5-(5-chloro-1-methyl-6-oxo-1,6-dihydro-pyridin-3-yl)-6-(4-chloro-phenyl)-1-isopropyl-4-oxo-1,4,5,6-tetrahydro-pyrrolo[3,4-b]pyrrole-3-carboxylic acid ethyl ester (Intermediate BM) 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=1.10 min (HPLC 3); ESI-MS: tR=1.05 min, [M+H]+ 626/628 (LC-MS 1); TLC: Rf=0.05 (EtOAc).

Workup

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

Sources & evidence

ORD record
ord-169dd914dad744c28396509800e1ca12
Source dataset
uspto-grants-2016_06
Patent number
US09365576B2

Reaction notes

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