Diisopropylethylamine → rac-2-(2-methyl-3-((2-oxopiperidin-3-yl)amino)quinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one

HRID 1056019Notes

Reaction equation

HRID 1056019 reaction equation
F[C:2]1[C:3]([CH3:22])=[N:4][C:5]2[C:10]([N:11]=1)=[C:9]([C:12]1[NH:20][C:19]3[CH2:18][CH2:17][NH:16][C:15](=[O:21])[C:14]=3[CH:13]=1)[CH:8]=[CH:7][CH:6]=2.Cl.N[N:25]1[CH2:30][CH2:29][CH2:28][CH2:27][C:26]1=[O:31].CC[N:34](C(C)C)C(C)C>>[CH3:22][C:3]1[C:2]([NH:34][CH:27]2[CH2:28][CH2:29][CH2:30][NH:25][C:26]2=[O:31])=[N:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[C:12]2[NH:20][C:19]3[CH2:18][CH2:17][NH:16][C:15](=[O:21])[C:14]=3[CH:13]=2)[N:4]=1

Participants

4

Reactant 3

HCID 81531DiisopropylethylamineHCID 668394931-Aminopiperidin-2-one hydrochlorideHCID 897833202-(3-fluoro-2-methylquinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one

Product 1

HCID 89784537rac-2-(2-methyl-3-((2-oxopiperidin-3-yl)amino)quinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-oneYield 33%

Conditions

Temperature
100 °C

Procedure

Prepared similar to that described in Example 131 using 2-(3-fluoro-2-methylquinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (Example 126; 42 mg, 0.142 mmol), rac-aminopiperidin-2-one hydrochloride (42.7 mg, 0.283 mmol, Matrix Scientific, Inc., Columbia, S.C.), and DIPEA (123 μl, 0.709 mmol), heating at 100° C. for 1.5 h. Purification by rpHPLC (Phenomenex Gemini C18, 10 μm, 150×30 mm; 10-100% ACN/water with 0.1% TFA) and silica gel (100% DCM to 10% MeOH/DCM) provided rac-2-(2-methyl-3-((2-oxopiperidin-3-yl)amino)quinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (33% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.82-2.01 (m, 3H) 2.27-2.37 (m, 1H) 2.57 (s, 3H) 2.83-2.91 (m, 2H) 3.21-3.29 (m, 2H) 3.45 (td, J=6.94, 2.35 Hz, 2H) 4.63-4.72 (m, 1H) 6.94 (s, 1H) 7.05-7.13 (m, 2H) 7.36 (t, J=7.82 Hz, 1H) 7.60 (dd, J=8.02, 1.17 Hz, 1H) 7.82-7.89 (m, 2H) 11.85 (br. s., 1H). MS (ESI, pos. ion) m/z: 391.1 (M+1).

Workup

  1. customPrepared similar to
  2. customPurification by rpHPLC (Phenomenex Gemini C18, 10 μm, 150×30 mm; 10-100% ACN/water with 0.1% TFA) and silica gel (100% DCM to 10% MeOH/DCM)

Sources & evidence

ORD record
ord-d9d58e322f8c4023836815407a03bdb3
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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