Hydrochloric Acid → 1-(9-Methyl-5,7,8,9-tetrahydro-6H-pyrido[3',4':4,5]pyrrolo[2,3-b]pyridin-2-yl)-4-(6-(trifluoromethyl)pyridin-3-yl)pyridin-2(1H)-one hydrochloride

HRID 882031Notes

Reaction equation

HRID 882031 reaction equation
[CH3:1][N:2]1[C:6]2=[N:7][C:8]([N:11]3[CH:16]=[CH:15][C:14]([C:17]4[CH:18]=[N:19][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:21][CH:22]=4)=[CH:13][C:12]3=[O:27])=[CH:9][CH:10]=[C:5]2[C:4]2[CH2:28][NH:29][CH2:30][CH2:31][C:3]1=2.[ClH:32]>CO.CCOCC>[ClH:32].[CH3:1][N:2]1[C:6]2=[N:7][C:8]([N:11]3[CH:16]=[CH:15][C:14]([C:17]4[CH:18]=[N:19][C:20]([C:23]([F:24])([F:25])[F:26])=[CH:21][CH:22]=4)=[CH:13][C:12]3=[O:27])=[CH:9][CH:10]=[C:5]2[C:4]2[CH2:28][NH:29][CH2:30][CH2:31][C:3]1=2

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 575245831-(9-Methyl-5,7,8,9-tetrahydro-6H-pyrido[3',4':4,5]pyrrolo[2,3-b]pyridin-2-yl)-4-(6-(trifluoromethyl)pyridin-3-yl)pyridin-2(1H)-one

Product 1

HCID 679701011-(9-Methyl-5,7,8,9-tetrahydro-6H-pyrido[3',4':4,5]pyrrolo[2,3-b]pyridin-2-yl)-4-(6-(trifluoromethyl)pyridin-3-yl)pyridin-2(1H)-one hydrochlorideYield 55%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

A solution of 1-(9-methyl-5,7,8,9-tetrahydro-6H-pyrido[3′,4′:4,5]pyrrolo[2,3-b]pyridin-2-yl)-4-(6-(trifluoromethyl)pyridin-3-yl)pyridin-2(1H)-one (0.49 g, 1.2 mmol) in MeOH (4.0 mL) was treated with 1.25 M HCl in MeOH (0.92 mL, 1.2 mmol), and the resulting suspension was stirred at ambient temperature for 4 h. The suspension was diluted with Et2O (50 mL) the resulting solids were collected by filtration, washed with CH2Cl2 (60 mL), and Et2O to provide the title compound (0.30 g, 55%) as a yellow powder: 307-316° C. decomp.; 1H NMR (500 MHz, DMSO-d6) δ 9.38 (s, 2H), 9.21 (d, J=2.5 Hz, 1H), 8.51 (dd, J=8.0, 2.0 Hz, 1H), 8.12 (d, J=8.5 Hz, 1H), 8.09-8.04 (m, 2H), 7.46 (d, J=8.0 Hz, 1H), 7.04 (d, J=2.0 Hz, 1H), 6.86 (dd, J=7.5, 2.0 Hz, 1H), 4.37 (s, 2H), 3.74 (s, 3H), 3.55 (t, J=6.5 Hz, 2H), 3.15 (t, J=6.0 Hz, 2H); ESI MS m/z 426 [M+H]+; HPLC (Method A)>99% (AUC), tR=13.1 min.

Workup

  1. filtrationwere collected by filtration
  2. washwashed with CH2Cl2 (60 mL), and Et2O

Sources & evidence

ORD record
ord-894da3dcf023409e930fd11672557348
Source dataset
uspto-grants-2015_03
Patent number
US08993765B2

Reaction notes

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