Acetate → 2-(4-(5-(5-(4-(2-Hydroxy-2-methylpropyl)piperazin-1-yl)pyridin-2-ylamino)-1-methyl-6-oxo-1,6-dihydropyridin-3-yl)-3-(hydroxymethyl)pyridin-2-yl)-3,4,6,7,8,9-hexahydropyrazino[1,2-a]indol-1(2H)-one

HRID 1021663Notes

Reaction equation

HRID 1021663 reaction equation
C1(C2NN=C(NC3C(=O)N(C)C=C(C4C=CN=C(N5CCN6C7CCCCC=7C=C6C5=O)C=4CO)C=3)C=2)CC1.C([O-])(=O)C.C([O:47][CH2:48][C:49]1[C:50]([N:81]2[CH2:93][CH2:92][N:84]3[C:85]4[CH2:86][CH2:87][CH2:88][CH2:89][C:90]=4[CH:91]=[C:83]3[C:82]2=[O:94])=[N:51][CH:52]=[CH:53][C:54]=1[C:55]1[CH:60]=[C:59]([NH:61][C:62]2[CH:67]=[CH:66][C:65]([N:68]3[CH2:73][CH2:72][N:71]([CH2:74][C:75]([OH:78])([CH3:77])[CH3:76])[CH2:70][CH2:69]3)=[CH:64][N:63]=2)[C:58](=[O:79])[N:57]([CH3:80])[CH:56]=1)(=O)C.O[Li].O>CC(O)C.C1COCC1.O>[OH:78][C:75]([CH3:77])([CH3:76])[CH2:74][N:71]1[CH2:72][CH2:73][N:68]([C:65]2[CH:66]=[CH:67][C:62]([NH:61][C:59]3[C:58](=[O:79])[N:57]([CH3:80])[CH:56]=[C:55]([C:54]4[CH:53]=[CH:52][N:51]=[C:50]([N:81]5[CH2:93][CH2:92][N:84]6[C:85]7[CH2:86][CH2:87][CH2:88][CH2:89][C:90]=7[CH:91]=[C:83]6[C:82]5=[O:94])[C:49]=4[CH2:48][OH:47])[CH:60]=3)=[N:63][CH:64]=2)[CH2:69][CH2:70]1

Participants

7

Reactant 4

HCID 175AcetateHCID 168937Lithium hydroxide, monohydrateHCID 715592982-(4-(5-(5-Cyclopropyl-1H-pyrazol-3-ylamino)-1-methyl-6-oxo-1,6-dihydropyridin-3-yl)-3-(hydroxymethyl)pyridin-2-yl)-3,4,6,7,8,9-hexahydropyrazino[1,2-a]indol-1(2H)-oneHCID 86684209(4-(5-(5-(4-(2-Hydroxy-2-methylpropyl)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 866842102-(4-(5-(5-(4-(2-Hydroxy-2-methylpropyl)piperazin-1-yl)pyridin-2-ylamino)-1-methyl-6-oxo-1,6-dihydropyridin-3-yl)-3-(hydroxymethyl)pyridin-2-yl)-3,4,6,7,8,9-hexahydropyrazino[1,2-a]indol-1(2H)-oneYield 42%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 22597222Tetrahydrofuran 2-propanolSolvent

Procedure

Following the procedures as described for the preparation of 118, acetate hydrolysis of 120b (70 mg, 0.1 mmol) with LiOH.H2O in iPrOH/THF (1:1) and H2O, gave 120 (27 mg, 42%) as a gray solid. LCMS: [M+H]+ 653. 1H NMR (500 MHz, DMSO-d6) δ 8.61 (d, J=3, 1H), 8.50 (d, J=5, 1H), 8.41 (s, 1H), 7.83 (d, J=3, 1H), 7.46 (d, J=2, 1H), 7.36 (m, 2H), 7.24 (d, J=9, 1H), 6.58 (s, 1H), 4.95 (m, 1H), 4.44 (m, 2H), 4.24 (m, 2H), 4.13 (m, 2H), 3.87-3.88 (m, 1H), 3.60 (s, 3H), 3.03-3.05 (m, 4H), 2.64-2.66 (m, 5H), 2.61-2.63 (m, 1H), 2.49-2.51 (m, 2H), 2.24 (s, 2H), 1.70-1.71 (m, 4H), 1.10 (s, 6H).

Sources & evidence

ORD record
ord-2b593071d15b496886d1ddc945178381
Source dataset
uspto-grants-2014_05
Patent number
US08716274B2

Reaction notes

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