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

HRID 1056023Notes

Reaction equation

FC1C(C)=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.NC1CCCC(O)C1>>[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

Reactant 2

HCID 112404593-Aminocyclohexanol

HCID 897833202-(3-fluoro-2-methylquinoxalin-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 17%

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) and 3-aminocyclohexanol (37.0 mg, 0.324 mmol, AB Chem, Inc., Dorval, Canada; mixture of racemic cis- and trans-isomers) and heating at 100° C. for 2 h. Purification by silica gel (100% DCM to 8% MeOH/DCM) provided 2434(3-hydroxycyclohexyl)amino)-2-methylquinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (17% yield; mixture of racemic cis- and trans-isomers). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.12-1.27 (m, 1H) 1.32-1.51 (m, 3H) 1.55-1.69 (m, 1H) 1.70-1.83 (m, 1H) 1.87 (d, J=12.72 Hz, 1H) 2.00 (br. s., 2H) 2.27 (d, J=11.93 Hz, 1H) 2.55 (d, J=4.11 Hz, 3H) 2.86-3.05 (m, 3H) 3.41-3.72 (m, 4H) 4.02-4.48 (m, 2H) 4.69-4.83 (m, 1H) 6.73-7.02 (m, 2H) 7.07-7.18 (m, 1H) 7.32 (td, J=7.82, 2.15 Hz, 1H) 7.53-7.60 (m, 1H) 7.85-7.96 (m, 1H) 11.86-12.16 (m, 1H). MS (ESI, pos. ion) m/z: 392 (M+1).

Workup

customPrepared similarly to that
customPurification by silica gel (100% DCM to 8% MeOH/DCM)

Sources & evidence

ORD record: ord-50d7fcb563334c3ab55bbc0190afe446
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09394297B2

Reaction notes

Loading…