Hydrochloric Acid → 2-methyl-2-((3-methyl-8-(4-oxo-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridin-2-yl)quinoxalin-2-yl)amino)propanoic acid

HRID 1055888Notes

Reaction equation

[CH3:1][C:2]([C:26]([O:28]C)=[O:27])([CH3:25])[NH:3][C:4]1[C:13]([CH3:14])=[N:12][C:11]2[C:6](=[C:7]([C:15]3[NH:23][C:22]4[CH2:21][CH2:20][NH:19][C:18](=[O:24])[C:17]=4[CH:16]=3)[CH:8]=[CH:9][CH:10]=2)[N:5]=1.[Li+].[OH-].CO.Cl>[NH4+].[Cl-]>[CH3:25][C:2]([NH:3][C:4]1[C:13]([CH3:14])=[N:12][C:11]2[C:6](=[C:7]([C:15]3[NH:23][C:22]4[CH2:21][CH2:20][NH:19][C:18](=[O:24])[C:17]=4[CH:16]=3)[CH:8]=[CH:9][CH:10]=2)[N:5]=1)([CH3:1])[C:26]([OH:28])=[O:27]

Participants

Conditions

Temperature: 25 °C

Procedure

A suspension of methyl 2-methyl-N-(3-methyl-8-(4-oxo-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridin-2-yl)-2-quinoxalinyl)alaninate (Ex. 57, 160 mg, 0.407 mmol), LiOH (51.2 mg, 1.220 mmol), and MeOH (2 mL) was stirred at 25° C. for 16 h. The reaction was then diluted with saturated aq. NH4Cl (10 mL) and neutralized to ˜pH 6 with 5 N HCl (aq). The resulting solution was extracted with 15% IPA:CHCl3 (3×30 mL) and the combined organic extracts were dried over Na2SO4, filtered, and concentrated under reduced pressure to provide 2-methyl-2-((3-methyl-8-(4-oxo-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridin-2-yl)quinoxalin-2-yl)amino)propanoic acid ((145 mg, 94%). 1H NMR (MeOH-d4) δ: 7.93-7.98 (m, 1H), 7.58-7.62 (m, 1H), 7.32-7.38 (m, 1H), 6.95 (s, 1H), 3.57-3.62 (m, 2H), 3.17-3.22 (m, 2H), 2.63-2.67 (m, 3H), 1.73-1.76 (m, 6H). m/z (ESI, +ve) 380.1 (M+H)+.

Workup

extractionThe resulting solution was extracted with 15% IPA
dry with materialCHCl3 (3×30 mL) and the combined organic extracts were dried over Na2SO4
filtrationfiltered
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-d7d9c7e7d9d14753bc680b9870c6ff96
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09394297B2

Reaction notes

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