2-Methoxypyrimidine-5-boronic acid → 5-(5-Chloro-1-methyl-6-oxo-1,6-dihydropyridin-3-yl)-6-(4-chlorophenyl)-1-cyclopropyl-2-(2-methoxypyrimidin-5-yl)-5,6-dihydropyrrolo[3,4-b]pyrrol-4(1H)-one

HRID 2204429Notes

Reaction equation

HRID 2204429 reaction equation
Br[C:2]1[N:6]([CH:7]2[CH2:9][CH2:8]2)[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[CH:19]=[C:18]([Cl:20])[C:17](=[O:21])[N:16]([CH3:22])[CH:15]=3)[C:12](=[O:13])[C:4]=2[CH:3]=1.[CH3:30][O:31][C:32]1[N:37]=[CH:36][C:35](B(O)O)=[CH:34][N:33]=1.C(Cl)Cl.CO.N>>[Cl:20][C:18]1[C:17](=[O:21])[N:16]([CH3:22])[CH:15]=[C:14]([N:11]2[C:12](=[O:13])[C:4]3[CH:3]=[C:2]([C:35]4[CH:34]=[N:33][C:32]([O:31][CH3:30])=[N:37][CH:36]=4)[N:6]([CH:7]4[CH2:9][CH2:8]4)[C:5]=3[CH:10]2[C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=2)[CH:19]=1

Participants

4

Reactant 3

HCID 27367782-Methoxypyrimidine-5-boronic acidHCID 21584172Ammonia methanol dichloromethaneHCID 867032482-bromo-5-(5-chloro-1-methyl-6-oxo-1,6-dihydropyridin-3-yl)-6-(4-chlorophenyl)-1-cyclopropyl-5,6-dihydropyrrolo[3,4-b]pyrrol-4(1H)-one

Product 1

HCID 867032515-(5-Chloro-1-methyl-6-oxo-1,6-dihydropyridin-3-yl)-6-(4-chlorophenyl)-1-cyclopropyl-2-(2-methoxypyrimidin-5-yl)-5,6-dihydropyrrolo[3,4-b]pyrrol-4(1H)-one

Procedure

The title compound was prepared in analogy to the procedure described in Example 240 but using 2-bromo-5-(5-chloro-1-methyl-6-oxo-1,6-dihydropyridin-3-yl)-6-(4-chlorophenyl)-1-cyclopropyl-5,6-dihydropyrrolo[3,4-b]pyrrol-4(1H)-one (Step 243.1) and (2-methoxypyrimidin-5-yl)boronic acid. tR: 0.97 min (LC-MS 6); ESI-MS: 522.1 [M+H]+ (LC-MS 6); TLC (CH2Cl2/MeOH/NH3 94:5:1): Rf=0.38; 1H NMR (400 MHz, DMSO-d6) δ ppm 0.18-0.40 (m, 1 H) 0.60-0.85 (m, 2 H) 1.09-1.19 (m, 1 H) 3.10-3.20 (m, 1 H) 3.42 (s, 3 H) 3.92 (s, 3 H) 6.33 (s, 1 H) 6.62 (s, 1 H) 7.32 (m, J=8.60 Hz, 2 H) 7.40 (m, J=8.60 Hz, 2 H) 7.80-7.97 (m, 2 H) 8.81 (s, 2 H).

Sources & evidence

ORD record
ord-79e984099ecf44b1a42e4e0966625e93
Source dataset
uspto-grants-2016_06
Patent number
US09365576B2

Reaction notes

Loading…