Diisopropylethylamine → HCID 89783605, compound

HRID 1056042Notes

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.CN.C[CH2:27][N:28](C(C)C)C(C)C>>[CH3:22][C:3]1[C:2]([NH:28][CH3:27])=[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 6364545Methylamine hydrochloride

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

Product 1

HCID 89783605HCID 89783605, compoundYield 16%

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; 67 mg, 0.226 mmol), methanamine hydrochloride (30.5 mg, 0.452 mmol; Sigma-Aldrich), and DIPEA (197 μl, 1.131 mmol), heating at 100° C. for 3 h. Purification by silica gel (100% DCM to 5% 2 M NH3 in MeOH/DCM) provided 2-(2-methyl-3-(methylamino)quinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (16% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 2.53 (s, 3H) 2.88 (t, J=6.85 Hz, 2H) 3.05 (d, J=4.50 Hz, 3H) 3.43 (td, J=6.80, 2.25 Hz, 2H) 6.94-6.98 (m, 1H) 7.13 (d, J=1.96 Hz, 1H) 7.32 (t, J=7.73 Hz, 1H) 7.37-7.43 (m, 1H) 7.58 (d, J=6.85 Hz, 1H) 7.90 (d, J=6.46 Hz, 1H) 12.24 (br. s., 1H). MS (ESI, pos. ion) m/z: 308.1 (M+1).

Workup

customPrepared similarly to that
customPurification by silica gel (100% DCM to 5% 2 M NH3 in MeOH/DCM)

Sources & evidence

ORD record: ord-e97afcb3536d4d02a62e19e1b89de23b
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09394297B2

Reaction notes

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