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)methoxy)pyridin-2(1H)-one hydrochloride

HRID 882035Notes

Reaction equation

HRID 882035 reaction equation
[CH3:1][N:2]1[C:6]2=[N:7][C:8]([N:11]3[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]4[CH:20]=[N:21][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:23][CH:24]=4)=[CH:13][C:12]3=[O:29])=[CH:9][CH:10]=[C:5]2[C:4]2[CH2:30][NH:31][CH2:32][CH2:33][C:3]1=2.[ClH:34]>CO.CCOCC>[ClH:34].[CH3:1][N:2]1[C:6]2=[N:7][C:8]([N:11]3[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]4[CH:20]=[N:21][C:22]([C:25]([F:27])([F:26])[F:28])=[CH:23][CH:24]=4)=[CH:13][C:12]3=[O:29])=[CH:9][CH:10]=[C:5]2[C:4]2[CH2:30][NH:31][CH2:32][CH2:33][C:3]1=2

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 575245841-(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)methoxy)pyridin-2(1H)-one

Product 1

HCID 679702261-(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)methoxy)pyridin-2(1H)-one hydrochlorideYield 78%

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)methoxy)pyridin-2(1H)-one (0.27 g, 0.59 mmol) in MeOH (2.0 mL) was treated with 1.25 M HCl in MeOH (0.47 mL, 0.59 mmol), and the resulting suspension was stirred at ambient temperature for 6 h. The suspension was diluted with Et2O, and the resulting solids were collected by filtration. The filtrate was concentrated, and the resulting residue was dissolved in CH2Cl2 (0.5 mL) and diluted with Et2O (50 mL). The resulting solids were collected by filtration. The solids from both batches were combined in Et2O and the resulting slurry was concentrated to dryness to provide the title compound (0.23 g, 78%) as an off-white powder: 280-278° C. decomp.; 1H NMR (500 MHz, DMSO-d6) δ 8.89 (d, J=1.0 Hz, 1H), 8.19 (d, J=8.0, 1.5 Hz, 1H), 8.17-7.80 (m, 4H), 7.33 (d, J=8.5 Hz, 1H), 6.21 (dd, J=7.5, 2.5 Hz, 1H), 6.04 (d, J=2.5 Hz, 1H), 5.36 (s, 2H), 4.22 (s, 2H), 3.69 (s, 3H), 3.41 (t, J=6.0 Hz, 2H), 3.01 (t, J=5.5 Hz, 2H); ESI MS m/z 456 [M+H]; HPLC (Method A)>99% (AUC), tR=13.4 min.

Workup

  1. filtrationthe resulting solids were collected by filtration
  2. concentrationThe filtrate was concentrated
  3. dissolutionthe resulting residue was dissolved in CH2Cl2 (0.5 mL)
  4. additiondiluted with Et2O (50 mL)
  5. filtrationThe resulting solids were collected by filtration
  6. concentrationthe resulting slurry was concentrated to dryness

Sources & evidence

ORD record
ord-8e0f3b9a7ae3453db6b1e1177a87407f
Source dataset
uspto-grants-2015_03
Patent number
US08993765B2

Reaction notes

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