Diisopropylethylamine → HCID 71731020, compound

HRID 1056021Notes

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([NH2:28])[CH2:27][CH2:26]1.CCN(C(C)C)C(C)C>>[CH3:22][C:3]1[C:2]([NH:28][C:25]2([CH3:24])[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

Reactant 3

HCID 81531Diisopropylethylamine

HCID 12953687(1-Methylcyclopropyl)amine hydrochloride

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

Product 1

HCID 71731020HCID 71731020, compoundYield 25%

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), 1-methylcyclopropanamine hydrochloride (34.9 mg, 0.324 mmol, ChemBridge, San Diego, Calif.), and DIPEA (141 μl, 0.810 mmol), heating at 100° C. for 2 h. Purification by silica gel (100% DCM to 6% MeOH/DCM) provided 2-(2-methyl-3-((1-methylcyclopropyl)amino)quinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (25% yield). 1H NMR (400 MHz, MeOH-d4) δ ppm 0.93-1.00 (m, 2H) 1.01-1.07 (m, 2H) 1.66 (s, 3H) 2.53 (s, 3H) 3.03 (t, J=7.04 Hz, 2H) 3.64 (t, J=7.04 Hz, 2H) 7.11 (s, 1H) 7.39 (t, J=7.92 Hz, 1H) 7.61 (d, J=8.02 Hz, 1H) 8.00 (d, J=7.63 Hz, 1H). MS (ESI, pos. ion) m/z: 348.2 (M+1).

Workup

customPrepared similarly to that
customPurification by silica gel (100% DCM to 6% MeOH/DCM)

Sources & evidence

ORD record: ord-9e873be61eaf498b896168835d725ca3
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09394297B2

Reaction notes

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