Pyridine → Trifluoroacetic acid

HRID 713299Notes

Reaction equation

HRID 713299 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[OH:8][C:9]([C:11]([F:14])([F:13])[F:12])=[O:10].[F:15][C:16]1[CH:42]=[C:41]([O:43][CH3:44])[CH:40]=[CH:39][C:17]=1[O:18][CH:19]1[CH2:24][CH2:23][N:22]([C:25]2[N:30]=[C:29]3[CH2:31][NH:32][CH2:33][CH2:34][C:28]3=[N:27][C:26]=2[NH:35][CH:36]([CH3:38])[CH3:37])[CH2:21][CH2:20]1.N1C=CC=CC=1>C(Cl)Cl>[F:15][C:16]1[CH:42]=[C:41]([O:43][CH3:44])[CH:40]=[CH:39][C:17]=1[O:18][CH:19]1[CH2:20][CH2:21][N:22]([C:25]2[N:30]=[C:29]3[CH2:31][N:32]([C:1](=[O:3])[CH3:2])[CH2:33][CH2:34][C:28]3=[N:27][C:26]=2[NH:35][CH:36]([CH3:38])[CH3:37])[CH2:23][CH2:24]1.[C:9]([OH:10])([C:11]([F:14])([F:13])[F:12])=[O:8]

Participants

6

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 131734029HCID 131734029, compound

Product 2

HCID 6422Trifluoroacetic acidYield 460.4%HCID 118159169HCID 118159169, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Acetic anhydride (9 μL, 0.095 mmol) was added to a solution of 3-(4-(2-fluoro-4-methoxyphenoxy)piperidin-1-yl)-N-isopropyl-5,6,7,8-tetrahydropyrido[3,4-b]pyrazin-2-amine TFA salt (25.2 mg, 0.048 mmol) and pyridine (11.5 μL, 0.143 mmol) in DCM (500 μL) at rt. After 1 h, the mixture was purified by HPLC Method A to give the title compound as a TFA salt (25.2 mg, 93%) as a yellow film. 1H NMR (400 MHz, methanol-d4, mixture of rotamers) δ ppm 1.32 (d, J=6.6 Hz, 6H), 1.89-2.00 (m, 2H), 2.06-2.15 (m, 2H), 2.19 (s, 1.4H), 2.21 (s, 1.6H), 2.77-2.83 (m, 0.9H), 2.87-2.93 (m, 1.1H), 3.04-3.14 (m, 2H), 3.42-3.50 (m, 2H), 3.75 (s, 3H), 3.80-3.85 (m, 1.1H), 3.85-3.90 (m, 0.9H), 4.09-4.19 (m, 1H), 4.35-4.42 (m, 1H), 4.55 (br s, 2H), 6.67 (dt, J=9.0, 1.4 Hz, 1H), 6.74 (dd, J=12.8, 2.9 Hz, 1H), 7.08 (t, J=9.2 Hz, 1H); ESI-MS m/z [M+H]+ 458.4.

Workup

  1. customthe mixture was purified by HPLC Method A

Sources & evidence

ORD record
ord-a5e7414f421a423db52c92ac88a5a045
Source dataset
uspto-grants-2015_11
Patent number
US09181249B2

Reaction notes

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