2-(3-fluoro-2-methylquinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one → HCID 178432138, compound

HRID 1056025Notes

Reaction equation

HRID 1056025 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.[NH2:23][C@H:24]1[CH2:29][CH2:28][C@H:27]([OH:30])[CH2:26][CH2:25]1>>[OH:30][C@H:27]1[CH2:28][CH2:29][C@H:24]([NH:23][C:2]2[C:3]([CH3:22])=[N:4][C:5]3[C:10]([N:11]=2)=[C:9]([C:12]2[NH:20][C:19]4[CH2:18][CH2:17][NH:16][C:15](=[O:21])[C:14]=4[CH:13]=2)[CH:8]=[CH:7][CH:6]=3)[CH2:25][CH2:26]1

Participants

3

Reactant 2

HCID 897833202-(3-fluoro-2-methylquinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-oneHCID 178511715HCID 178511715, compound

Product 1

HCID 178432138HCID 178432138, compoundYield 54%

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) and trans-4-aminocyclohexanol (32.7 mg, 0.283 mmol; Alfa Aesar, Ward Hill, Mass.), heating at 100° C. for 1 h. Purification by silica gel (100% DCM to 10% MeOH/DCM) provided 2-(3-((trans-4-hydroxycyclohexyl)amino)-2-methylquinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (54% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.34-1.57 (m, 4H) 1.93 (d, J=11.54 Hz, 2H) 2.09 (d, J=12.32 Hz, 2H) 2.54 (s, 3H) 2.92 (t, J=6.85 Hz, 2H) 3.42-3.54 (m, 3H) 3.91-4.04 (m, 1H) 4.60 (br. s., 1H) 6.75 (d, J=7.43 Hz, 1H) 6.94 (s, 1H) 7.08 (d, J=2.15 Hz, 1H) 7.32 (t, J=7.82 Hz, 1H) 7.57 (dd, J=8.02, 1.37 Hz, 1H) 7.89 (dd, J=7.53, 1.27 Hz, 1H) 11.96 (br. s., 1H). MS (ESI, pos. ion) m/z: 392.3 (M+1).

Workup

  1. customPrepared similarly to that
  2. customPurification by silica gel (100% DCM to 10% MeOH/DCM)

Sources & evidence

ORD record
ord-e6798698465f4372864a9c1c9648897f
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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