Diisopropylethylamine → 1H,4H,5H,6H,7H-pyrrolo[3,2-c]pyridin-4-one

HRID 1056033Notes

Reaction equation

HRID 1056033 reaction equation
FC1C=NC2C(N=1)=C([C:12]1[NH:20][C:19]3[CH2:18][CH2:17][NH:16][C:15](=[O:21])[C:14]=3[CH:13]=1)C=CC=2.Cl.CC1(N)CC1.CCN(C(C)C)C(C)C>>[NH:20]1[C:19]2[CH2:18][CH2:17][NH:16][C:15](=[O:21])[C:14]=2[CH:13]=[CH:12]1

Participants

4

Reactant 3

HCID 81531DiisopropylethylamineHCID 12953687(1-Methylcyclopropyl)amine hydrochlorideHCID 897843702-(3-fluoroquinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one

Product 1

HCID 220385131H,4H,5H,6H,7H-pyrrolo[3,2-c]pyridin-4-oneYield 21%

Conditions

Temperature
100 °C

Procedure

Prepared similarly to that described in Example 210 using 2-(3-fluoroquinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (Example 210i; 72 mg, 0.255 mmol), 1-methylcyclopropanamine hydrochloride (54.9 mg, 0.510 mmol, ChemBridge, San Diego, Calif.), and DIPEA (223 μl, 1.275 mmol), heating at 100° C. for 1 h. Purification by silica gel (100% DCM to 4% MeOH/DCM) provided 2434(1-methylcyclopropyl)amino)-quinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (21% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 0.89 (s, 4H) 1.54 (s, 3H) 2.93 (t, J=6.85 Hz, 2H) 3.46 (td, J=6.85, 2.35 Hz, 2H) 6.99 (br. s., 1H) 7.15 (d, J=1.56 Hz, 1H) 7.37 (t, J=7.82 Hz, 1H) 7.63 (dd, J=8.02, 0.98 Hz, 1H) 8.05 (dd, J=7.63, 1.17 Hz, 1H) 8.33 (s, 2H) 12.89 (br. s., 1H). MS (ESI, pos. ion) m/z: 334.1 (M+1).

Workup

  1. customPrepared similarly to that
  2. customPurification by silica gel (100% DCM to 4% MeOH/DCM)

Sources & evidence

ORD record
ord-061375c7e79741faa0f7518e10d8a3d3
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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