(5-Cyano-2-Methoxyphenyl)Boronic Acid → HCID 72204596, compound

HRID 2204368Notes

Reaction equation

HRID 2204368 reaction equation
BrC1N(C(C)C)C2C(C3C=CC(Cl)=CC=3)N(C3C=CC([F:20])=C(Cl)C=3)C(=O)C=2C=1.[Cl:29][C:30]1[CH:31]=[CH:32][C:33](C)=[C:34]([N:36]2[C:43](=[O:44])[C:42]3[CH:41]=[C:40]([C:45]4[C:46]([O:53][CH3:54])=NC(OC)=N[CH:50]=4)[N:39]([CH:55]([CH3:57])[CH3:56])[C:38]=3[C@H:37]2[C:58]2[CH:63]=[CH:62][C:61]([Cl:64])=[CH:60][CH:59]=2)[CH:35]=1.Br[C:67]1N(C(C)C)C2[CH:75](C3C=CC(Cl)=CC=3)[N:76](C3C=C(Cl)C=CC=3C)[C:77](=[O:78])[C:69]=2[CH:68]=1.C(C1C=CC(OC)=C(B(O)O)C=1)#N>>[Cl:29][C:30]1[CH:35]=[C:34]([N:36]2[C:43](=[O:44])[C:42]3[CH:41]=[C:40]([C:45]4[CH:50]=[C:69]([CH:68]=[CH:67][C:46]=4[O:53][CH3:54])[C:77]([NH:76][CH3:75])=[O:78])[N:39]([CH:55]([CH3:57])[CH3:56])[C:38]=3[CH:37]2[C:58]2[CH:59]=[CH:60][C:61]([Cl:64])=[CH:62][CH:63]=2)[CH:33]=[CH:32][C:31]=1[F:20]

Participants

5

Reactant 4

HCID 23005336(5-Cyano-2-Methoxyphenyl)Boronic AcidHCID 72206456(R)-5-(5-Chloro-2-methyl-phenyl)-6-(4-chloro-phenyl)-2-(2,4-dimethoxy-pyrimidin-5-yl)-1-isopropyl-5,6-dihydro-1H-pyrrolo[3,4-b]pyrrol-4-one2×HCID 867030982-Bromo-5-(3-chloro-4-fluoro-phenyl)-6-(4-chloro-phenyl)-1-isopropyl-5,6-dihydro-1H-pyrrolo[3,4-b]pyrrol-4-one2×HCID 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 72204596HCID 72204596, compound

Procedure

The title compound was prepared in analogy to the procedure described for Example 17 but 2-bromo-5-(3-chloro-4-fluoro-phenyl)-6-(4-chloro-phenyl)-1-isopropyl-5,6-dihydro-1H-pyrrolo[3,4-b]pyrrol-4-one (Intermediate D) and 2-methoxy-5-[(methylamino)carbonyl]phenylboronic acid (Intermediate R) 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: 7.27 min (HPLC 2); ESI-MS: tR=1.24 min, [M+H]+ 566/568/570 (LC-MS 1); TLC: Rf=0.07 (98:2 CH2Cl2/MeOH).

Workup

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

Sources & evidence

ORD record
ord-db27f3c1ba2949cfb55ed8a4e478bca1
Source dataset
uspto-grants-2016_06
Patent number
US09365576B2

Reaction notes

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