Hydrochloric Acid → 1-(6-Methyl-1,2,3,4,5,6-hexahydroazepino[4,3-b]indol-8-yl)-4-((6-methylpyridin-3-yl)methoxy)pyridin-2(1H)-one hydrochloride

HRID 474923Notes

Reaction equation

HRID 474923 reaction equation
[CH3:1][N:2]1[C:10]2[CH:9]=[C:8]([N:11]3[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]4[CH:20]=[N:21][C:22]([CH3:25])=[CH:23][CH:24]=4)=[CH:13][C:12]3=[O:26])[CH:7]=[CH:6][C:5]=2[C:4]2[CH2:27][N:28](C(OC(C)(C)C)=O)[CH2:29][CH2:30][CH2:31][C:3]1=2.[ClH:39]>CO>[ClH:39].[CH3:1][N:2]1[C:10]2[CH:9]=[C:8]([N:11]3[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]4[CH:20]=[N:21][C:22]([CH3:25])=[CH:23][CH:24]=4)=[CH:13][C:12]3=[O:26])[CH:7]=[CH:6][C:5]=2[C:4]2[CH2:27][NH:28][CH2:29][CH2:30][CH2:31][C:3]1=2

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 70805195tert-Butyl 6-methyl-8-(4-((6-methyl pyridine-3-yl)methoxy)-2-oxopyridin-1(2H)-yl)-3,4,5,6-tetrahydroazepino[4,3-b]indole-2(1H)-carboxylate

Product 1

HCID 668737381-(6-Methyl-1,2,3,4,5,6-hexahydroazepino[4,3-b]indol-8-yl)-4-((6-methylpyridin-3-yl)methoxy)pyridin-2(1H)-one hydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

tert-Butyl 6-methyl-8-(4-((6-methyl pyridine-3-yl)methoxy)-2-oxopyridin-1(2H)-yl)-3,4,5,6-tetrahydroazepino[4,3-b]indole-2(1H)-carboxylate (0.12 g, 0.22 mmol) was treated with 1.25 M HCl in MeOH (13 mL), and the resulting solution was stirred at ambient temperature for 18 h. The solution was concentrated to dryness to provide the title compound (0.10 g, quantitative) as a brown solid: 1H NMR (500 MHz, DMSO-d6) δ 9.17 (s, 2H), 8.89 (s, 1H), 8.51 (d, J=8.0 Hz, 1H), 7.94 (d, J=8.0 Hz, 1H), 7.65 (d, J=8.5 Hz, 1H), 7.61 (d, J=7.5 Hz, 1H), 7.47 (d, J=1.5 Hz, 1H), 6.98 (dd, J=8.5, 1.5 Hz, 1H), 6.14 (dd, J=8.0, 2.5 Hz, 1H), 6.03 (d, J=2.0 Hz, 1H), 5.33 (s, 2H), 4.44-4.41 (m, 2H), 3.71 (s, 3H), 3.44-3.42 (m, 2H), 3.10-3.08 (m, 2H), 2.76 (s, 3H), 2.08-2.04 (m, 2H); ESI MS m/z 415 [M+H]+; HPLC (Method A)>99% (AUC), tR=9.4 min.

Workup

  1. concentrationThe solution was concentrated to dryness

Sources & evidence

ORD record
ord-26f39c165b9544f4894e1ded11e32577
Source dataset
uspto-grants-2014_01
Patent number
US08637501B2

Reaction notes

Loading…