Ammonia methanol dichloromethane → 5-(5-Chloro-1-methyl-6-oxo-1,6-dihydropyridin-3-yl)-6-(4-chlorophenyl)-1-cyclopropyl-2-(1-methyl-2-oxo-1,2-dihydropyridin-4-yl)-5,6-dihydropyrrolo[3,4-b]pyrrol-4(1H)-one

HRID 2204427Notes

Reaction equation

HRID 2204427 reaction equation
[CH3:1][N:2]1[CH:7]=[CH:6][C:5](B2OC(C)(C)C(C)(C)O2)=[CH:4][C:3]1=[O:17].Br[C:19]1[N:23]([CH:24]2[CH2:26][CH2:25]2)[C:22]2[CH:27]([C:40]3[CH:45]=[CH:44][C:43]([Cl:46])=[CH:42][CH:41]=3)[N:28]([C:31]3[CH:36]=[C:35]([Cl:37])[C:34](=[O:38])[N:33]([CH3:39])[CH:32]=3)[C:29](=[O:30])[C:21]=2[CH:20]=1.C(Cl)Cl.CO.N>>[Cl:37][C:35]1[C:34](=[O:38])[N:33]([CH3:39])[CH:32]=[C:31]([N:28]2[C:29](=[O:30])[C:21]3[CH:20]=[C:19]([C:5]4[CH:6]=[CH:7][N:2]([CH3:1])[C:3](=[O:17])[CH:4]=4)[N:23]([CH:24]4[CH2:26][CH2:25]4)[C:22]=3[CH:27]2[C:40]2[CH:41]=[CH:42][C:43]([Cl:46])=[CH:44][CH:45]=2)[CH:36]=1

Participants

4

Reactant 3

HCID 21584172Ammonia methanol dichloromethaneHCID 457865301-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)pyridin-2(1H)-oneHCID 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 867032475-(5-Chloro-1-methyl-6-oxo-1,6-dihydropyridin-3-yl)-6-(4-chlorophenyl)-1-cyclopropyl-2-(1-methyl-2-oxo-1,2-dihydropyridin-4-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 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2(1H)-one (Step 242.1) and 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 250.1). tR: 0.83 min (LC-MS 6); ESI-MS: 521.2/523.2 [M+H]+ (LC-MS 6); TLC (CH2Cl2/MeOH/NH3 94:5:1): Rf=0.18; 1H NMR (400 MHz, DMSO-d6) δ ppm 0.35-0.450 (m, 1 H) 0.74-0.84 (m, 2 H) 1.12-1.25 (m, 1 H) 3.06-3.18 (m, 1 H) 3.41 (s, 3 H) 3.37 (s, 3 H) 6.30 (s, 1 H) 6.47 (dd, J=7.04, 1.95 Hz, 1 H) 6.52-6.61 (m, 1 H) 6.71 (s, 1 H) 7.30 (m, J=8.21 Hz, 2 H) 7.38 (m, J=8.60 Hz, 2 H) 7.62 (d, J=7.04 Hz, 1 H) 7.80-7.95 (m, 2 H).

Sources & evidence

ORD record
ord-181feee139bd468fb04c87978d227e93
Source dataset
uspto-grants-2016_06
Patent number
US09365576B2

Reaction notes

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