5-Bromo-3-(5-((2S,5R)-2,5-dimethyl-4-(oxetan-3-yl)piperazin-1-yl)-pyridin-2-ylamino)-1-methylpyridin-2(1H)-one → (4-(5-(5-((2S,5R)-2,5-Dimethyl-4-(oxetan-3-yl)piperazin-1-yl)pyridin-2-ylamino)-1-methyl-6-oxo-1,6-dihydropyridin-3-yl)-2-(1-oxo-3,4,6,7,8,9-hexahydropyrazino[1,2-a]indol-2(1H)-yl)pyridin-3-yl)methyl Acetate

HRID 592606Notes

Reaction equation

HRID 592606 reaction equation
[C:1]([O:4][CH2:5][C:6]1[C:7]([N:31]2[CH2:43][CH2:42][N:34]3[C:35]4[CH2:36][CH2:37][CH2:38][CH2:39][C:40]=4[CH:41]=[C:33]3[C:32]2=[O:44])=[N:8][CH:9]=[CH:10][C:11]=1C1C=C(NC2C=C3CN(C)CCN3N=2)C(=O)N(C)C=1)(=[O:3])[CH3:2].Br[C:46]1[CH:47]=[C:48]([NH:54][C:55]2[CH:60]=[CH:59][C:58]([N:61]3[CH2:66][C@@H:65]([CH3:67])[N:64]([CH:68]4[CH2:71][O:70][CH2:69]4)[CH2:63][C@@H:62]3[CH3:72])=[CH:57][N:56]=2)[C:49](=[O:53])[N:50]([CH3:52])[CH:51]=1.C(OCC1C(N2CCN3C4CCCCC=4C=C3C2=O)=NC=CC=1B1OC(C)(C)C(C)(C)O1)(=O)C>>[C:1]([O:4][CH2:5][C:6]1[C:7]([N:31]2[CH2:43][CH2:42][N:34]3[C:35]4[CH2:36][CH2:37][CH2:38][CH2:39][C:40]=4[CH:41]=[C:33]3[C:32]2=[O:44])=[N:8][CH:9]=[CH:10][C:11]=1[C:46]1[CH:47]=[C:48]([NH:54][C:55]2[CH:60]=[CH:59][C:58]([N:61]3[CH2:66][C@@H:65]([CH3:67])[N:64]([CH:68]4[CH2:71][O:70][CH2:69]4)[CH2:63][C@@H:62]3[CH3:72])=[CH:57][N:56]=2)[C:49](=[O:53])[N:50]([CH3:52])[CH:51]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 3

HCID 866837065-Bromo-3-(5-((2S,5R)-2,5-dimethyl-4-(oxetan-3-yl)piperazin-1-yl)-pyridin-2-ylamino)-1-methylpyridin-2(1H)-oneHCID 86684143(2-(1-oxo-3,4,6,7,8,9-hexahydropyrazino[1,2-a]indol-2(1H)-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)methyl acetateHCID 86684195(4-(1-Methyl-5-(5-methyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazin-2-ylamino)-6-oxo-1,6-dihydropyridin-3-yl)-2-(1-oxo-3,4,6,7,8,9-hexahydropyrazino[1,2-a]indol-2(1H)-yl)pyridin-3-yl)methyl acetate

Product 1

HCID 86684215(4-(5-(5-((2S,5R)-2,5-Dimethyl-4-(oxetan-3-yl)piperazin-1-yl)pyridin-2-ylamino)-1-methyl-6-oxo-1,6-dihydropyridin-3-yl)-2-(1-oxo-3,4,6,7,8,9-hexahydropyrazino[1,2-a]indol-2(1H)-yl)pyridin-3-yl)methyl AcetateYield 41%

Procedure

Following the procedures as described for compound 113j, reaction of 122e (723 mg, 1.62 mmol) and 3-(acetoxymethyl)-2-(1-oxo-3,4,6,7,8,9-hexahydropyrazino[1,2-a]indol-2(1H)-yl)pyridin-4-ylboronic acid 113i (613 mg, 1.62 mmol) afforded 122f as a yellow solid (464 mg, 41%). LCMS: [M+H]+ 707

Sources & evidence

ORD record
ord-34b2bf48c4844e2da583b2627145d559
Source dataset
uspto-grants-2016_01
Patent number
US09238655B2

Reaction notes

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