Ammonium Hydroxide → HCID 89783894, compound

HRID 1056041Notes

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.[NH4+:23].[OH-]>CC(O)C>[NH2:23][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

Participants

Conditions

Temperature: 120 °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; 51 mg, 0.172 mmol) and NH4OH (670 μl, 17.21 mmol) in propan-2-ol (1.7 ml) and heating in a microwave reactor (Biotage Initiator) at 120° C. for 10 min. Purification by silica gel (100% DCM to 5% MeOH/DCM) provided 2-(3-amino-2-methylquinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (61% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 2.52 (s, 3H) 2.94 (t, J=6.85 Hz, 2H) 3.44 (td, J=6.80, 2.25 Hz, 2H) 6.94 (br. s., 1H) 6.98 (d, J=2.15 Hz, 1H) 7.15 (br. s., 2H) 7.29 (t, J=7.82 Hz, 1H) 7.54 (dd, J=8.02, 0.98 Hz, 1H) 7.91 (dd, J=7.53, 1.08 Hz, 1H) 12.45 (br. s., 1H). MS (ESI, pos. ion) m/z: 294.0 (M+1).

Workup

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

Sources & evidence

ORD record: ord-77eed080347e44b89860055b0c096904
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09394297B2

Reaction notes

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