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

HRID 1056022Notes

Reaction equation

HRID 1056022 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.[CH3:24][C:25]1([NH2:31])[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1.CCN(C(C)C)C(C)C>>[CH3:22][C:3]1[C:2]([NH:31][C:25]2([CH3:24])[CH2:30][CH2:29][O:28][CH2:27][CH2:26]2)=[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 184373724-Methyloxan-4-amine hydrochlorideHCID 897833202-(3-fluoro-2-methylquinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one

Product 1

HCID 897842352-(2-methyl-3-((4-methyltetrahydro-2H-pyran-4-yl)amino)quinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-oneYield 6%

Conditions

Temperature
100 °C

Procedure

Prepared similarly 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; 48 mg, 0.162 mmol), 4-methyltetrahydro-2H-pyran-4-amine hydrochloride (49.1 mg, 0.324 mmol, Biofine International, Blaine, Wash.), and DIPEA (141 μl, 0.810 mmol), heating at 100° C. for 20 h. Purification by silica gel (100% DCM to 5% MeOH/DCM) provided 2-(2-methyl-3-((4-methyltetrahydro-2H-pyran-4-yl)amino)quinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (6% yield). 1H NMR (400 MHz, MeOD) δ ppm 1.73 (s, 3H) 1.85-1.95 (m, 2H) 2.53 (d, J=13.50 Hz, 2H) 2.67 (s, 3H) 3.01 (t, J=7.14 Hz, 2H) 3.64 (t, J=7.14 Hz, 2H) 3.76-3.82 (m, 4H) 7.00 (s, 1H) 7.40 (t, J=7.82 Hz, 1H) 7.65 (dd, J=8.12, 1.27 Hz, 1H) 7.88 (dd, J=7.53, 1.27 Hz, 1H). MS (ESI, pos. ion) m/z: 392.1 (M+1).

Workup

  1. customPrepared similarly to that
  2. customPurification by silica gel (100% DCM to 5% MeOH/DCM)

Sources & evidence

ORD record
ord-36a4d10081cf46bfa441e4f8b27b8d74
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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