HCID 53630359, compound → HCID 72205158, compound

HRID 2204371Notes

Reaction equation

HRID 2204371 reaction equation
Br[C:2]1[N:6]([CH:7]([CH3:9])[CH3:8])[C:5]2[CH:10]([C:23]3[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=3)[N:11]([C:14]3[C:15](=[O:22])[N:16]([CH3:21])[CH:17]=[C:18]([Cl:20])[CH:19]=3)[C:12](=[O:13])[C:4]=2[CH:3]=1.[CH3:30][O:31][C:32]1C=[C:36]([O:38][CH3:39])[C:35](B(O)O)=[CH:34][N:33]=1.BrC1[N:48](C(C)C)C2C(C3C=CC(Cl)=CC=3)N(C3C=C(Cl)C=CC=3C)C(=O)C=2C=1.COC1C(B2OC(C)(C)C(C)(C)O2)=CN=C(N)N=1>>[Cl:20][C:18]1[CH:19]=[C:14]([N:11]2[C:12](=[O:13])[C:4]3[CH:3]=[C:2]([C:35]4[C:36]([O:38][CH3:39])=[N:48][C:32]([O:31][CH3:30])=[N:33][CH:34]=4)[N:6]([CH:7]([CH3:9])[CH3:8])[C:5]=3[CH:10]2[C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=2)[C:15](=[O:22])[N:16]([CH3:21])[CH:17]=1

Participants

5

Reactant 4

HCID 53630359HCID 53630359, compoundHCID 591984044-Methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-amineHCID 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 86703172HCID 86703172, compound2×

Product 1

HCID 72205158HCID 72205158, compound

Procedure

The title compound was prepared in analogy to the procedure described for Example 25 but 2-bromo-5-(5-chloro-1-methyl-2-oxo-1,2-dihydro-pyridin-3-yl)-6-(4-chloro-phenyl)-1-isopropyl-5,6-dihydro-1H-pyrrolo[3,4-b]pyrrol-4-one (Intermediate L) and 2,4-dimethoxypyridine-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 4-methoxy-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyrimidin-2-ylamine respectively. The title compound was obtained as a white solid. ESI-MS: tR=1.12 min, [M+H]+ 554/556/558 (LC-MS 1); 1H-NMR (d6-DMSO, 400 MHz): 8.29 (s, 1H), 7.87 (m, 1H), 7.36-7.43 (m, 3H), 7.22 (m, 2H), 6.65 (s, 1H), 6.34 (s, 1H), 3.94 (m, 1H), 3.93 (s, 3H), 3.89 (s, 3H), 3.42 (s, 3H), 1.29 (m, 3H), 0.46 (m, 3H).

Workup

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

Sources & evidence

ORD record
ord-54c4b1c7347942e3a204953cd3a15e1d
Source dataset
uspto-grants-2016_06
Patent number
US09365576B2

Reaction notes

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