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

HRID 882044Notes

Reaction equation

HRID 882044 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][CH: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.[ClH:32]>CO>[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]=[CH: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

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 573839591-(9-Methyl-5,7,8,9-tetrahydro-6H-pyrido[3',4':4,5]pyrrolo[2,3-b]pyridin-2-yl)-4-(4-(trifluoromethyl)phenyl)pyridin-2(1H)-one

Product 1

HCID 679700521-(9-Methyl-5,7,8,9-tetrahydro-6H-pyrido[3',4':4,5]pyrrolo[2,3-b]pyridin-2-yl)-4-(4-(trifluoromethyl)phenyl)pyridin-2(1H)-one hydrochlorideYield 82%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

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-(4-(trifluoromethyl)phenyl)pyridin-2(1H)-one (50 mg, 0.12 mmol) in MeOH (2.0 mL) was treated with 1.25 M HCl in MeOH (94 μL, 0.12 mmol), and the resulting solution was stirred at ambient temperature for 18 h. The solution was concentrated to dryness to provide the title compound (45 mg, 82%) as a bright yellow powder: mp 278-281° C. decomp.; 1H NMR (500 MHz, DMSO-d6) δ 8.06-8.00 (m, 4H), 7.88 (d, J=8.0 Hz, 2H), 7.42 (d, J=3.0 Hz, 1H), 6.90 (d, J=2.0 Hz, 1H), 6.78 (dd, J=7.0, 2.0 Hz, 1H), 4.19 (s, 2H), 3.71 (s, 3H), 3.37 (t, J=5.5 Hz, 2H), 2.99 (t, J=5.5 Hz, 2H); ESI MS m/z 425 [M+H]+; HPLC (Method A) 98.9% (AUC), tR=14.8 min.

Workup

  1. concentrationThe solution was concentrated to dryness

Sources & evidence

ORD record
ord-6ff6f3e189d743068895716fc1ccf05b
Source dataset
uspto-grants-2015_03
Patent number
US08993765B2

Reaction notes

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