Lithium Hydroxide → 2-(4-(5-(6,7-Dihydro-4H-pyrazolo[5,1-c][1,4]oxazin-2-ylamino)-1-methyl-6-oxo-1,6-dihydropyridazin-3-yl)-3-(hydroxymethyl)pyridin-2-yl)-3,4,6,7,8,9-hexahydropyrazino[1,2-a]indol-1(2H)-one

HRID 592647Notes

Reaction equation

HRID 592647 reaction equation
C([C@H]1CN(C2COC2)CCN1C1C=CC(NC2C(=O)N(C)C=C(C3C=CN=C(N4CCN5C6CCCCC=6C=C5C4=O)C=3CO)C=2)=NC=1)C.C([O:53][CH2:54][C:55]1[C:56]([N:79]2[CH2:91][CH2:90][N:82]3[C:83]4[CH2:84][CH2:85][CH2:86][CH2:87][C:88]=4[CH:89]=[C:81]3[C:80]2=[O:92])=[N:57][CH:58]=[CH:59][C:60]=1[C:61]1[CH:66]=[C:65]([NH:67][C:68]2[CH:76]=[C:71]3[CH2:72][O:73][CH2:74][CH2:75][N:70]3[N:69]=2)[C:64](=[O:77])[N:63]([CH3:78])[N:62]=1)(=O)C.[OH-].[Li+]>>[N:69]1[N:70]2[C:71]([CH2:72][O:73][CH2:74][CH2:75]2)=[CH:76][C:68]=1[NH:67][C:65]1[C:64](=[O:77])[N:63]([CH3:78])[N:62]=[C:61]([C:60]2[CH:59]=[CH:58][N:57]=[C:56]([N:79]3[CH2:91][CH2:90][N:82]4[C:83]5[CH2:84][CH2:85][CH2:86][CH2:87][C:88]=5[CH:89]=[C:81]4[C:80]3=[O:92])[C:55]=2[CH2:54][OH:53])[CH:66]=1

Participants

4

Reactant 3

HCID 3939Lithium HydroxideHCID 86684231(S)-2-(4-(5-(5-(2-ethyl-4-(oxetan-3-yl)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)-oneHCID 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 Acetate

Product 1

HCID 866842342-(4-(5-(6,7-Dihydro-4H-pyrazolo[5,1-c][1,4]oxazin-2-ylamino)-1-methyl-6-oxo-1,6-dihydropyridazin-3-yl)-3-(hydroxymethyl)pyridin-2-yl)-3,4,6,7,8,9-hexahydropyrazino[1,2-a]indol-1(2H)-oneYield 65%

Procedure

Following the procedures as described for compound 131, hydrolysis of 132b (100 mg 0.171 mmol) with lithium hydroxide afforded 132 as a white solid (60 mg, 65%). LCMS: [M+H]+ 543. 1H NMR (500 MHz, CDCl3) δ 8.55 (d, J=5.0, 1H), 8.01 (s, 1H), 7.94 (s, 1H), 7.43 (d, J=5.5, 1H), 6.87 (s, 1H), 5.97 (s, 1H), 4.80 (s, 2H), 4.58 (s, 3H), 4.47 (s, 1H), 4.15-1.14 (m, 2H), 4.11 (s, 4H), 3.90 (s, 4H), 2.61-2.60 (m, 2H), 2.57 (t, J=6.5, 2H), 1.89-1.91 (m, 2H), 1.79-1.80 (m, 2H)

Sources & evidence

ORD record
ord-12ae4393e8604bd8bab24820511ddbb7
Source dataset
uspto-grants-2016_01
Patent number
US09238655B2

Reaction notes

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