Formaldehyde → Trifluoroacetic acid

HRID 713313Notes

Reaction equation

HRID 713313 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:37]=[C:36]([F:38])[CH:35]=[CH:34][C:33]=1[CH:39]([F:60])[CH:40]1[CH2:45][CH2:44][N:43]([C:46]2[N:51]=[C:50]3[CH2:52][NH:53][CH2:54][CH2:55][C:49]3=[N:48][C:47]=2[NH:56][CH:57]([CH3:59])[CH3:58])[CH2:42][CH2:41]1.C=O>CO>[F:31][C:32]1[CH:37]=[C:36]([F:38])[CH:35]=[CH:34][C:33]=1[CH:39]([F:60])[CH:40]1[CH2:45][CH2:44][N:43]([C:46]2[N:51]=[C:50]3[CH2:52][N:53]([CH3:1])[CH2:54][CH2:55][C:49]3=[N:48][C:47]=2[NH:56][CH:57]([CH3:58])[CH3:59])[CH2:42][CH2:41]1.[C:25]([OH:26])([C:27]([F:30])([F:29])[F:28])=[O:24]

Participants

7

Reactant 4

HCID 712FormaldehydeHCID 81531DiisopropylethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 131734035HCID 131734035, compound

Product 2

HCID 6422Trifluoroacetic acidYield 470.2%HCID 118159372HCID 118159372, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium triacetoxyborohydride (15.3 mg, 0.072 mmol) was added to a mixture of DIPEA (9.4 mg, 0.072 mmol), 3-(4-((2,4-difluorophenyl)fluoromethyl)piperidin-1-yl)-N-isopropyl-5,6,7,8-tetrahydropyrido[3,4-b]pyrazin-2-amine TFA salt (19.3 mg, 0.036 mmol) and formaldehyde (3 μL, 0.036 mmol) in MeOH (360 μL) at rt. After 30 min, the mixture was purified by HPLC Method A to give the title compound as a TFA salt (19.3 mg, 97%) as a yellow film. 1H NMR (400 MHz, methanol-d4) δ ppm 1.24 (dd, J=6.4, 2.2 Hz, 6H), 1.40-1.48 (m, 1H), 1.53-1.74 (m, 2H), 1.96-2.14 (m, 2H), 2.60-2.73 (m, 2H), 2.93-3.06 (br m, 2H), 3.06 (s, 3H), 3.39-3.54 (m, 3H), 3.69-3.81 (m, 1H), 4.18 (dt, J=13.1, 6.4 Hz, 2H), 4.16-4.36 (br m, 1H), 5.52 (dd, J=46.2, 7.6 Hz, 1H), 6.97-7.08 (m, 2H), 7.47-7.54 (m, 1H); ESI-MS m/z [M+H]+ 434.4.

Workup

  1. customthe mixture was purified by HPLC Method A

Sources & evidence

ORD record
ord-b4053aefa92f4b0a9849a0994eba8fc4
Source dataset
uspto-grants-2015_11
Patent number
US09181249B2

Reaction notes

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