Formaldehyde → Trifluoroacetic acid

HRID 713326Notes

Reaction equation

HRID 713326 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].[F:18][C:19]1[CH:45]=[C:44]([F:46])[CH:43]=[CH:42][C:20]=1[O:21][CH:22]1[CH2:27][CH2:26][N:25]([C:28]2[N:29]=[C:30]3[CH2:41][CH2:40][NH:39][CH2:38][C:31]3=[N:32][C:33]=2[NH:34][CH:35]([CH3:37])[CH3:36])[CH2:24][CH2:23]1.C=O>CO>[F:18][C:19]1[CH:45]=[C:44]([F:46])[CH:43]=[CH:42][C:20]=1[O:21][CH:22]1[CH2:23][CH2:24][N:25]([C:28]2[N:29]=[C:30]3[CH2:41][CH2:40][N:39]([CH3:2])[CH2:38][C:31]3=[N:32][C:33]=2[NH:34][CH:35]([CH3:37])[CH3:36])[CH2:26][CH2:27]1.[C:12]([OH:13])([C:14]([F:17])([F:16])[F:15])=[O:11]

Participants

7

Reactant 4

HCID 712FormaldehydeHCID 81531DiisopropylethylamineHCID 5360545SodiumHCID 1317340252-(4-(2,4-difluorophenoxy)piperidin-1-yl)-N-isopropyl-5,6,7,8-tetrahydropyrido[3,4-b]pyrazin-3-amine TFA salt

Product 2

HCID 6422Trifluoroacetic acidYield 339.4%HCID 118159398HCID 118159398, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium triacetoxyhydroborate (9.9 mg, 0.047 mmol) was added to a solution of DIPEA (8 μL, 0.047 mmol), 2-(4-(2,4-difluorophenoxyl)piperidin-1-yl)-N-isopropyl-5,6,7,8-tetrahydropyrido[3,4-b]pyrazin-3-amine TFA salt (12.1 mg, 0.023 mmol) and formaldehyde (2 μL, 0.023 mmol) in MeOH (230 μL) at rt. After 30 min, the mixture was purified by HPLC Method A to give the title compound as a TFA salt (8.9 mg, 71.6%) as a yellow film. 1H NMR (400 MHz, methanol-d4) δ ppm 1.24 (d, J=6.3 Hz, 6H), 1.90-2.00 (m, 2H), 2.08-2.17 (m, 2H), 2.95-3.06 (m, 3H), 3.12 (br s, 4H), 3.35-3.53 (m, 3H), 3.76 (br s, 1H), 4.15 (dt, J=13.1, 6.5, 6.5 Hz, 1H), 4.19-4.38 (m, 2H), 4.48 (tt, J=7.3, 3.7 Hz, 1H), 6.85-6.92 (m, 1H), 6.99 (ddd, J=11.4, 8.5, 3.0 Hz, 1H), 7.17 (td, J=9.2, 5.6 Hz, 1H); ESI-MS m/z [M+H]+ 418.3.

Workup

  1. customthe mixture was purified by HPLC Method A

Sources & evidence

ORD record
ord-d68aa77a3be84f088416079464c70967
Source dataset
uspto-grants-2015_11
Patent number
US09181249B2

Reaction notes

Loading…