Propylamine → HCID 89783564, compound

HRID 1056011Notes

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.[CH2:23]([NH2:26])[CH2:24][CH3:25]>>[CH3:22][C:3]1[C:2]([NH:26][CH2:23][CH2:24][CH3:25])=[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

Reactant 2

HCID 7852Propylamine

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

Product 1

HCID 89783564HCID 89783564, compoundYield 57%

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; 50 mg, 0.169 mmol) and propan-1-amine (41.6 μl, 0.506 mmol, Aldrich), heating at 100° C. for 2 h. Purification by silica gel (100% DCM to 5% MeOH/DCM) provided 2-(2-methyl-3-(propylamino)quinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (57% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.07 (t, J=7.34 Hz, 3H) 1.80 (sxt, J=7.39 Hz, 2H) 2.58 (s, 3H) 2.93 (t, J=6.85 Hz, 2H) 3.46-3.57 (m, 4H) 6.98 (br. s., 1H) 7.20 (d, J=2.35 Hz, 1H) 7.34-7.43 (m, 2H) 7.61 (dd, J=8.02, 1.17 Hz, 1H) 7.93 (d, J=7.63 Hz, 1H) 12.19 (br. s., 1H). MS (ESI, pos. ion) m/z: 336.2 (M+1).

Workup

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

Sources & evidence

ORD record: ord-e7e948faf16e436dafe006d9a7241781
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09394297B2

Reaction notes

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