Formaldehyde → Trifluoroacetic acid

HRID 713306Notes

Reaction equation

HRID 713306 reaction equation
[C:1](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].CCN(C(C)C)C(C)C.[OH:24][C:25]([C:27]([F:30])([F:29])[F:28])=[O:26].[F:31][C:32]1[CH:58]=[C:57]([O:59][CH3:60])[CH:56]=[CH:55][C:33]=1[O:34][CH:35]1[CH2:40][CH2:39][N:38]([C:41]2[N:46]=[C:45]3[CH2:47][NH:48][CH2:49][CH2:50][C:44]3=[N:43][C:42]=2[NH:51][CH:52]([CH3:54])[CH3:53])[CH2:37][CH2:36]1.C=O>CO>[F:31][C:32]1[CH:58]=[C:57]([O:59][CH3:60])[CH:56]=[CH:55][C:33]=1[O:34][CH:35]1[CH2:36][CH2:37][N:38]([C:41]2[N:46]=[C:45]3[CH2:47][N:48]([CH3:1])[CH2:49][CH2:50][C:44]3=[N:43][C:42]=2[NH:51][CH:52]([CH3:54])[CH3:53])[CH2:39][CH2:40]1.[C:25]([OH:26])([C:27]([F:30])([F:29])[F:28])=[O:24]

Participants

7

Reactant 4

HCID 712FormaldehydeHCID 81531DiisopropylethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 131734029HCID 131734029, compound

Product 2

HCID 6422Trifluoroacetic acidYield 461.7%HCID 118159341HCID 118159341, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium triacetoxyborohydride (22.3 mg, 0.105 mmol) was added to a mixture of DIPEA (18 μL, 0.105 mmol), 3-(4-(2-fluoro-4-methoxyphenoxy)piperidin-1-yl)-N-isopropyl-5,6,7,8-tetrahydropyrido[3,4-b]pyrazin-2-amine TFA salt (27.9 mg, 0.053 mmol) and formaldehyde (4 μL, 0.053 mmol) in MeOH (550 μL) at rt. After 30 min, the mixture was purified by HPLC Method A to give the title compound as a TFA salt (27.9 mg, 97%) as a yellow film. 1H NMR (400 MHz, methanol-d4) δ ppm 1.25 (d, J=6.3 Hz, 6H), 1.88-1.98 (m, 2H), 2.04-2.14 (m, 2H), 2.93-3.05 (m, 3H), 3.07 (br s, 4H), 3.33-3.40 (m, 2H), 3.41-3.69 (m, 2H), 3.75 (s, 3H), 4.15-4.32 (m, 3H), 4.32-4.39 (m, 1H), 6.66 (ddd, J=8.9, 3.0, 1.5 Hz, 1H), 6.73 (dd, J=12.8, 2.9 Hz, 1H), 7.07 (t, J=9.2 Hz, 1H); ESI-MS m/z [M+H]+ 430.4.

Workup

  1. customthe mixture was purified by HPLC Method A

Sources & evidence

ORD record
ord-ef52421d2da3462fac78c498246e3f8d
Source dataset
uspto-grants-2015_11
Patent number
US09181249B2

Reaction notes

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