Hydrochloric Acid → 1-(10-Methyl-5,6,7,8,9,10-hexahydropyrido[3',2':4,5]pyrrolo [2,3-d]azepin-2-yl)-4-(6-(trifluoromethyl)pyridazin-3-yl)pyridin-2(1H)-one hydrochloride

HRID 474974Notes

Reaction equation

HRID 474974 reaction equation
[ClH:1].[CH3:2][N:3]1[C:7]2[CH2:8][CH2:9][N:10](C(OC(C)(C)C)=O)[CH2:11][CH2:12][C:6]=2[C:5]2[CH:20]=[CH:21][C:22]([N:24]3[CH:29]=[CH:28][C:27]([C:30]4[N:31]=[N:32][C:33]([C:36]([F:39])([F:38])[F:37])=[CH:34][CH:35]=4)=[CH:26][C:25]3=[O:40])=[N:23][C:4]1=2>CO.CCOCC>[ClH:1].[CH3:2][N:3]1[C:7]2[CH2:8][CH2:9][NH:10][CH2:11][CH2:12][C:6]=2[C:5]2[CH:20]=[CH:21][C:22]([N:24]3[CH:29]=[CH:28][C:27]([C:30]4[N:31]=[N:32][C:33]([C:36]([F:39])([F:38])[F:37])=[CH:34][CH:35]=4)=[CH:26][C:25]3=[O:40])=[N:23][C:4]1=2

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 66874194tert-butyl 10-methyl-2-(2-oxo-4-(6-(trifluoromethyl)pyridazin-3-yl)pyridin-1(2H)-yl)-5,8,9,10-tetrahydropyrido[3',2':4,5]pyrrolo[2,3-d]azepine-7(6H)-carboxylate

Product 1

HCID 668738911-(10-Methyl-5,6,7,8,9,10-hexahydropyrido[3',2':4,5]pyrrolo [2,3-d]azepin-2-yl)-4-(6-(trifluoromethyl)pyridazin-3-yl)pyridin-2(1H)-one hydrochlorideYield 94%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

1.25 M HCl in MeOH (4.3 mL) was added to tert-butyl 10-methyl-2-(2-oxo-4-(6-(trifluoromethyl)pyridazin-3-yl)pyridin-1(2H)-yl)-5,8,9,10-tetrahydropyrido[3′,2′:4,5]pyrrolo[2,3-d]azepine-7(6H)-carboxylate (47 mg, 0.087 mmol), and the resulting solution was stirred under N2 at ambient temperature for 20 h. The solution was diluted with Et2O (25 mL), and the resulting solids were collected by filtration to provide the title compound (39 mg, 94%) as a yellow solid: mp 300-305° C. dec; 1H NMR (500 MHz, DMSO-d6) δ 9.10 (s, 2H), 8.71 (d, J=9.0 Hz, 1H), 8.47 (d, J=9.0 Hz, 1H), 8.12-8.10 (m, 2H), 7.44 (d, J=8.0 Hz, 1H), 7.40 (d, J=2.0 Hz, 1H), 7.23 (dd, J=7.0, 2.0 Hz, 1H), 3.77 (s, 3H), 3.46-3.41 (m, 2H), 3.38-3.34 (m, 2H), 3.32-3.30 (m, 2H, overlapped with solvent), 3.17 (t, J=6.0 Hz, 2H); ESI MS m/z 441 [M+H]+; HPLC (Method A)>99% (AUC), tR=12.8 min.

Workup

  1. filtrationthe resulting solids were collected by filtration

Sources & evidence

ORD record
ord-248ef62ed36f41dda9a43b2f74f707cb
Source dataset
uspto-grants-2014_01
Patent number
US08637501B2

Reaction notes

Loading…