Lithium Hydroxide → 2-(4-(5-(6,7-Dihydro-4H-pyrazolo[5,1-c][1,4]oxazin-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 592640Notes

Reaction equation

HRID 592640 reaction equation
C([O:4][CH2:5][C:6]1[C:7]([N:30]2[CH2:42][CH2:41][N:33]3[C:34]4[CH2:35][CH2:36][CH2:37][CH2:38][C:39]=4[CH:40]=[C:32]3[C:31]2=[O:43])=[N:8][CH:9]=[CH:10][C:11]=1[C:12]1[CH:17]=[C:16]([NH:18][C:19]2[CH:27]=[C:22]3[CH2:23][O:24][CH2:25][CH2:26][N:21]3[N:20]=2)[C:15](=[O:28])[N:14]([CH3:29])[CH:13]=1)(=O)C.[OH-].[Li+]>>[N:20]1[N:21]2[C:22]([CH2:23][O:24][CH2:25][CH2:26]2)=[CH:27][C:19]=1[NH:18][C:16]1[C:15](=[O:28])[N:14]([CH3:29])[CH:13]=[C:12]([C:11]2[CH:10]=[CH:9][N:8]=[C:7]([N:30]3[CH2:42][CH2:41][N:33]4[C:34]5[CH2:35][CH2:36][CH2:37][CH2:38][C:39]=5[CH:40]=[C:32]4[C:31]3=[O:43])[C:6]=2[CH2:5][OH:4])[CH:17]=1

Participants

3

Reactant 2

HCID 3939Lithium HydroxideHCID 86684230(4-(5-(6,7-Dihydro-4H-pyrazolo[5,1-c][1,4]oxazin-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 715569552-(4-(5-(6,7-Dihydro-4H-pyrazolo[5,1-c][1,4]oxazin-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 62%

Procedure

Following the procedures as described in Example 113, 129d (180 mg 0.31 mmol) was hydrolyzed with lithium hydroxide to give 129 as a white solid (100 mg, 62%). LCMS: [M+H]+ 542. 1H NMR (500 MHz, CDCl3) δ 8.48 (d, J=5.0, 1H), 7.98 (d, J=2.0, 1H), 7.71 (d, J=2.0, 1H), 7.46 (s, 1H), 7.35 (d, J=5.0, 1H), 6.89 (s, 1H), 5.72 (s, 1H), 5.03 (d, J=6.5, 1H), 4.79 (s, 2H), 4.61-4.64 (m, 1H), 4.50 (s, 1H), 4.31-4.35 (m, 1H), 4.06-4.16 (m, 6H), 3.86 (s, 1H), 3.71 (s, 3H), 2.56-2.62 (m, 4H), 1.88-1.92 (m, 2H), 1.80 (m, 2H)

Sources & evidence

ORD record
ord-e4aaafdeeea744149de0b052f4ed53ec
Source dataset
uspto-grants-2016_01
Patent number
US09238655B2

Reaction notes

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