Pyridine → Trifluoroacetic acid

HRID 713321Notes

Reaction equation

HRID 713321 reaction equation
C(O[C:5](=[O:7])[CH3:6])(=O)C.[OH:8][C:9]([C:11]([F:14])([F:13])[F:12])=[O:10].[Cl:15][C:16]1[CH:17]=[CH:18][C:19]([F:44])=[C:20]([C:22]([CH:24]2[CH2:29][CH2:28][N:27]([C:30]3[N:35]=[C:34]4[CH2:36][NH:37][CH2:38][CH2:39][C:33]4=[N:32][C:31]=3[NH:40][CH:41]([CH3:43])[CH3:42])[CH2:26][CH2:25]2)=[O:23])[CH:21]=1.N1C=CC=CC=1>C(Cl)Cl>[Cl:15][C:16]1[CH:17]=[CH:18][C:19]([F:44])=[C:20]([CH:21]=1)[C:22]([CH:24]1[CH2:29][CH2:28][N:27]([C:30]2[N:35]=[C:34]3[CH2:36][N:37]([C:5](=[O:7])[CH3:6])[CH2:38][CH2:39][C:33]3=[N:32][C:31]=2[NH:40][CH:41]([CH3:42])[CH3:43])[CH2:26][CH2:25]1)=[O:23].[C:9]([OH:10])([C:11]([F:14])([F:13])[F:12])=[O:8]

Participants

6

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 131734037HCID 131734037, compound

Product 2

HCID 6422Trifluoroacetic acidYield 206.4%HCID 118159151HCID 118159151, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Acetic anhydride (3 μL, 0.034 mmol) was added to a solution of (5-chloro-2-fluorophenyl)(1-(2-(isopropylamino)-5,6,7,8-tetrahydropyrido[3,4-b]pyrazin-3-yl)piperidin-4-yl)methanone TFA salt (9.2 mg, 0.017 mmol) and pyridine (4 μL, 0.051 mmol) in DCM (170 μL) at rt. After 1 h, the mixture was purified by HPLC Method A to give the title compound as a TFA salt (4.0 mg, 40.4%) as a yellow film. 1H NMR (400 MHz, methanol-d4, mixture of rotamers) δ ppm 1.30-1.34 (m, 6H), 1.88-2.04 (m, 4H), 2.19 (s, 1.4H), 2.21 (s, 1.6H), 2.77-2.83 (m, 0.9H), 2.87-2.92 (m, 1.1H), 2.93-3.02 (m, 2H), 3.34-3.43 (m, 1H), 3.50-3.59 (m, 2H), 3.80-3.85 (m, 1.1H), 3.85-3.90 (m, 0.9H), 4.08-4.17 (m, 1H), 4.54 (br s, 2H), 7.25-7.32 (m, 1H), 7.59-7.63 (m, 1H), 7.76 (dd, J=6.1, 2.8 Hz, 1H); ESI-MS m/z [M+H]+ 474.3.

Workup

  1. customthe mixture was purified by HPLC Method A

Sources & evidence

ORD record
ord-40ff5131d7664a3f8dce4106b7b0295f
Source dataset
uspto-grants-2015_11
Patent number
US09181249B2

Reaction notes

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