Formaldehyde → Trifluoroacetic acid

HRID 713328Notes

Reaction equation

HRID 713328 reaction equation
[Na].[CH3:2]CN(C(C)C)C(C)C.[OH:11][C:12]([C:14]([F:17])([F:16])[F:15])=[O:13].[Cl:18][C:19]1[CH:20]=[CH:21][C:22]([F:47])=[C:23]([C:25]([CH:27]2[CH2:32][CH2:31][N:30]([C:33]3[N:34]=[C:35]4[CH2:46][CH2:45][NH:44][CH2:43][C:36]4=[N:37][C:38]=3[NH:39][CH:40]([CH3:42])[CH3:41])[CH2:29][CH2:28]2)=[O:26])[CH:24]=1.C=O>CO>[Cl:18][C:19]1[CH:20]=[CH:21][C:22]([F:47])=[C:23]([C:25]([CH:27]2[CH2:32][CH2:31][N:30]([C:33]3[N:34]=[C:35]4[CH2:46][CH2:45][N:44]([CH3:2])[CH2:43][C:36]4=[N:37][C:38]=3[NH:39][CH:40]([CH3:42])[CH3:41])[CH2:29][CH2:28]2)=[O:26])[CH:24]=1.[C:12]([OH:13])([C:14]([F:17])([F:16])[F:15])=[O:11]

Participants

7

Reactant 4

HCID 712FormaldehydeHCID 81531DiisopropylethylamineHCID 5360545SodiumHCID 131734038HCID 131734038, compound

Product 2

HCID 6422Trifluoroacetic acidYield 274.8%HCID 118159326HCID 118159326, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium triacetoxyhydroborate (6.5 mg, 0.031 mmol) was added to a solution of DIPEA (5 μL, 0.031 mmol), (5-chloro-2-fluorophenyl)(1-(3-(isopropylamino)-5,6,7,8-tetrahydropyrido[3,4-b]pyrazin-2-yl)piperidin-4-yl)methanone TFA salt (8.4 mg, 0.015 mmol) and formaldehyde (1.5 μL, 0.015 mmol) in MeOH (150 μL) at rt. After 30 min, the mixture was purified by HPLC Method A to give the title compound as a TFA salt (4.7 mg, 54.6%) as a yellow solid. 1H NMR (400 MHz, methanol-d4) δ ppm 1.24 (d, J=6.6 Hz, 6H), 1.82-1.93 (m, 2H), 1.97-2.05 (m, 2H), 2.81-3.05 (m, 4H), 3.08 (s, 3H), 3.35-3.54 (m, 4H), 3.72-3.83 (m, 1H), 4.10-4.18 (m, 1H), 4.19-4.40 (m, 2H), 7.25-7.32 (m, 1H), 7.61 (ddd, J=8.8, 4.3, 2.8 Hz, 1H), 7.75 (dd, J=6.1, 2.8 Hz, 1H); ESI-MS m/z [M+H]+ 446.3.

Workup

  1. customthe mixture was purified by HPLC Method A

Sources & evidence

ORD record
ord-fc68fec11f114f8487c87c934dbcc063
Source dataset
uspto-grants-2015_11
Patent number
US09181249B2

Reaction notes

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