6-Chloro-4-(6,7-dihydro-4H-pyrazolo[5,1-c][1,4]oxazin-2-ylamino)-2-methylpyridazin-3(2H)-one → (4-(5-(6,7-Dihydro-4H-pyrazolo[5,1-c][1,4]oxazin-2-ylamino)-1-methyl-6-oxo-1,6-dihydropyridazin-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 592648Notes

Reaction equation

HRID 592648 reaction equation
C(OCC1C(N2CCN3C4CCCCC=4C=C3C2=O)=NC=CC=1C1C=C(NC2C=CC(N3CCN(C4COC4)C[C@@H]3CC)=CN=2)C(=O)N(C)C=1)(=O)C.[C:53]([O:56][CH2:57][C:58]1[C:59]([N:73]2[CH2:85][CH2:84][N:76]3[C:77]4[CH2:78][CH2:79][CH2:80][CH2:81][C:82]=4[CH:83]=[C:75]3[C:74]2=[O:86])=[N:60][CH:61]=[CH:62][C:63]=1B1OC(C)(C)C(C)(C)O1)(=[O:55])[CH3:54].Cl[C:88]1[CH:89]=[C:90]([NH:96][C:97]2[CH:105]=[C:100]3[CH2:101][O:102][CH2:103][CH2:104][N:99]3[N:98]=2)[C:91](=[O:95])[N:92]([CH3:94])[N:93]=1>>[C:53]([O:56][CH2:57][C:58]1[C:59]([N:73]2[CH2:85][CH2:84][N:76]3[C:77]4[CH2:78][CH2:79][CH2:80][CH2:81][C:82]=4[CH:83]=[C:75]3[C:74]2=[O:86])=[N:60][CH:61]=[CH:62][C:63]=1[C:88]1[CH:89]=[C:90]([NH:96][C:97]2[CH:105]=[C:100]3[CH2:101][O:102][CH2:103][CH2:104][N:99]3[N:98]=2)[C:91](=[O:95])[N:92]([CH3:94])[N:93]=1)(=[O:55])[CH3:54]

Participants

4

Reactant 3

HCID 580437886-Chloro-4-(6,7-dihydro-4H-pyrazolo[5,1-c][1,4]oxazin-2-ylamino)-2-methylpyridazin-3(2H)-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 86684232(S)-(4-(5-(5-(2-ethyl-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

Product 1

HCID 86684233(4-(5-(6,7-Dihydro-4H-pyrazolo[5,1-c][1,4]oxazin-2-ylamino)-1-methyl-6-oxo-1,6-dihydropyridazin-3-yl)-2-(1-oxo-3,4,6,7,8,9-hexahydropyrazino[1,2-a]indol-2(1H)-yl)pyridin-3-yl)methyl AcetateYield 55.9%

Procedure

Following the procedures as described for compound 131a and starting with 3-(acetoxymethyl)-2-(1-oxo-3,4,6,7,8,9-hexahydropyrazino[1,2-a]indol-2(1H)-yl)pyridin-4-ylboronic acid 113i (200 mg, 0.52 mmol) and 132a (153 mg, 0.52 mmol) afforded 132b as a yellow solid (170 mg, 55%). LCMS: [M+H]+ 598

Sources & evidence

ORD record
ord-8dcead712b8e4ff2ba55f1a0f1f4ae3e
Source dataset
uspto-grants-2016_01
Patent number
US09238655B2

Reaction notes

Loading…