Lithium Hydroxide → 2-(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)-3-(hydroxymethyl)pyridin-2-yl)-3,4,6,7,8,9-hexahydropyrazino[1,2-a]indol-1(2H)-one

HRID 592607Notes

Reaction equation

OCC1C(N2CCN3C4CCCCC=4C=C3C2=O)=NC=CC=1C1C=C(NC2C=C3CN(C)CCN3N=2)C(=O)N(C)C=1.C([O:45][CH2:46][C:47]1[C:48]([N:80]2[CH2:92][CH2:91][N:83]3[C:84]4[CH2:85][CH2:86][CH2:87][CH2:88][C:89]=4[CH:90]=[C:82]3[C:81]2=[O:93])=[N:49][CH:50]=[CH:51][C:52]=1[C:53]1[CH:58]=[C:57]([NH:59][C:60]2[CH:65]=[CH:64][C:63]([N:66]3[CH2:71][C@@H:70]([CH3:72])[N:69]([CH:73]4[CH2:76][O:75][CH2:74]4)[CH2:68][C@@H:67]3[CH3:77])=[CH:62][N:61]=2)[C:56](=[O:78])[N:55]([CH3:79])[CH:54]=1)(=O)C.[OH-].[Li+]>>[CH3:77][C@H:67]1[CH2:68][N:69]([CH:73]2[CH2:76][O:75][CH2:74]2)[C@H:70]([CH3:72])[CH2:71][N:66]1[C:63]1[CH:64]=[CH:65][C:60]([NH:59][C:57]2[C:56](=[O:78])[N:55]([CH3:79])[CH:54]=[C:53]([C:52]3[CH:51]=[CH:50][N:49]=[C:48]([N:80]4[CH2:92][CH2:91][N:83]5[C:84]6[CH2:85][CH2:86][CH2:87][CH2:88][C:89]=6[CH:90]=[C:82]5[C:81]4=[O:93])[C:47]=3[CH2:46][OH:45])[CH:58]=2)=[N:61][CH:62]=1

Participants

Reactant 3

HCID 3939Lithium Hydroxide

HCID 715591542-(3-(Hydroxymethyl)-4-(1-methyl-5-(5-methyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazin-2-ylamino)-6-oxo-1,6-dihydropyridin-3-yl)pyridin-2-yl)-3,4,6,7,8,9-hexahydropyrazino[1,2-a]indol-1(2H)-one

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 Acetate

Product 1

HCID 715592992-(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)-3-(hydroxymethyl)pyridin-2-yl)-3,4,6,7,8,9-hexahydropyrazino[1,2-a]indol-1(2H)-oneYield 20%

Procedure

Following the procedures as described for compound 113, hydrolysis of 122f (464 mg, 0.66 mmol) with lithium hydroxide afforded 122 as a white solid (83 mg, 20%). LCMS: [M+H]+ 665. 1H NMR (500 MHz, CDCl3) δ 8.69 (d, J=2.5, 1H), 8.51 (d, J=5.0, 1H), 8.03 (d, J=2.5, 1H), 7.88 (s, 1H), 7.86 (d, J=2.5, 1H), 7.38 (d, J=5.0, 2H), 6.90 (s, 1H), 6.82 (d, J=9.0, 1H), 5.07 (s, 1H), 4.77-4.72 (m, 2H), 4.68-4.61 (m, 3H), 4.52 (s, 1H), 4.33 (s, 1H), 4.17-4.11 (m, 2H), 3.88 (s, 1H), 3.76 (s, 1H), 3.73 (s, 3H), 3.19 (s, 1H), 2.93-2.90 (m, 1H), 2.73 (s, 2H), 2.63-2.57 (m, 4H), 2.48 (s, 1H), 1.99-1.90 (m, 3H), 1.80 (s, 2H), 0.91 (t, J=5.5, 6H)

Sources & evidence

ORD record: ord-ede97e826f2b4497964704ed4ee41f14
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09238655B2

Reaction notes

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