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

HRID 882038Notes

Reaction equation

HRID 882038 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:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][N:18]=4)=[CH:13][C:12]3=[O:27])=[CH:9][CH:10]=[C:5]2[C:4]2[CH2:28][N:29](C(OC(C)(C)C)=O)[CH2:30][CH2:31][C:3]1=2.[ClH:39]>CO.CCOCC>[ClH:39].[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:22]=[CH:21][C:20]([C:23]([F:24])([F:25])[F:26])=[CH:19][N:18]=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 86667080tert-Butyl 9-methyl-2-(2-oxo-4-(5-(trifluoromethyl)pyridin-2-yl)pyridin-1(2H)-yl)-5,7,8,9-tetrahydro-6H-pyrido[3',4':4,5]pyrrolo[2,3-b]pyridine-6-carboxylate

Product 1

HCID 679710441-(9-Methyl-5,7,8,9-tetrahydro-6H-pyrido[3',4':4,5]pyrrolo[2,3-b]pyridin-2-yl)-4-(5-(trifluoromethyl)pyridin-2-yl)pyridin-2(1H)-one hydrochlorideYield 76%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

tert-Butyl 9-methyl-2-(2-oxo-4-(5-(trifluoromethyl)pyridin-2-yl)pyridin-1(2H)-yl)-5,7,8,9-tetrahydro-6H-pyrido[3′,4′:4,5]pyrrolo[2,3-b]pyridine-6-carboxylate (82 mg, 0.16 mmol) was treated with 1.25 M HCl in MeOH (5.0 mL), and the resulting solution was stirred at ambient temperature for 18 h. The solution was diluted with Et2O, and the resulting solids were collected by filtration to provide the title compound (55 mg, 76%) as a yellow solid: 298-302° C. decomp.; 1H NMR (500 MHz, DMSO-d6) δ 9.30 (br s, 1H), 9.15 (t, J=1.0 Hz, 1H), 8.42-8.34 (m, 2H), 8.13 (d, J=8.0 Hz, 1H), 8.08 (d, J=7.0 Hz, 1H), 7.49 (d, J=8.5 Hz, 1H), 7.32 (d, J=2.0 Hz, 1H), 7.13 (dd, J=7.0, 2.0 Hz, 1H), 4.39 (s, 2H), 3.74 (s, 3H), 3.60-3.51 (m, 2H), 3.15 (t, J=6.0 Hz, 2H); ESI MS m/z 426 [M+H]+; HPLC (Method A) 98.8% (AUC), tR=13.7 min.

Workup

  1. filtrationthe resulting solids were collected by filtration

Sources & evidence

ORD record
ord-abad584abf9c412ca5b4cc38e9c5c9e4
Source dataset
uspto-grants-2015_03
Patent number
US08993765B2

Reaction notes

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