Pyridine → Trifluoroacetic acid

HRID 713318Notes

Reaction equation

HRID 713318 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].[F:15][C:16]1[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:17]=1[CH:23]([F:44])[CH:24]1[CH2:29][CH2:28][N:27]([C:30]2[N:31]=[C:32]3[CH2:43][CH2:42][NH:41][CH2:40][C:33]3=[N:34][C:35]=2[NH:36][CH:37]([CH3:39])[CH3:38])[CH2:26][CH2:25]1.N1C=CC=CC=1>C(Cl)Cl>[F:15][C:16]1[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:17]=1[CH:23]([F:44])[CH:24]1[CH2:29][CH2:28][N:27]([C:30]2[N:31]=[C:32]3[CH2:43][CH2:42][N:41]([C:5](=[O:7])[CH3:6])[CH2:40][C:33]3=[N:34][C:35]=2[NH:36][CH:37]([CH3:39])[CH3:38])[CH2:26][CH2:25]1.[C:9]([OH:10])([C:11]([F:14])([F:13])[F:12])=[O:8]

Participants

6

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 131734036HCID 131734036, compound

Product 2

HCID 6422Trifluoroacetic acidYield 464.5%HCID 118159216HCID 118159216, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Acetic anhydride (5 μL, 0.054 mmol) was added to a solution of 2-(4-((2,4-difluorophenyl)fluoromethyl)piperidin-1-yl)-N-isopropyl-5,6,7,8-tetrahydropyrido[3,4-b]pyrazin-3-amine TFA salt (14.3 mg, 0.027 mmol) and pyridine (6.5 μL, 0.080 mmol) in DCM (270 μL) at rt. After 1 h, the mixture was purified by HPLC Method A to give the title compound as a TFA salt (14.3 mg, 93%) as a yellow film. 1H NMR (400 MHz, methanol-d4, mixture of rotamers) δ ppm 1.23-1.31 (m, 6H), 1.45 (d, J=12.9 Hz, 1H), 1.53-1.76 (m, 2H), 1.96-2.15 (m, 2H), 2.18 (s, 1.2H), 2.21 (s, 1.8H), 2.67-2.84 (m, 4H), 3.38-3.55 (m, 2H), 3.78-3.83 (m, 1.2H), 3.83-3.87 (m, 0.8H), 4.13 (dq, J=12.6, 6.3 Hz, 1H), 4.56 (s, 0.8H), 4.59 (s, 1.2H), 5.53 (dd, J=46.2, 7.6 Hz, 1H), 6.97-7.09 (m, 2H), 7.47-7.55 (m, 1H); ESI-MS m/z [M+H]+ 462.4.

Workup

  1. customthe mixture was purified by HPLC Method A

Sources & evidence

ORD record
ord-3eb409fd7b0c4b96b354135500f8c3ca
Source dataset
uspto-grants-2015_11
Patent number
US09181249B2

Reaction notes

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