Dimethylcarbamoyl Chloride → Trifluoroacetic acid

HRID 713315Notes

Reaction equation

HRID 713315 reaction equation
[CH3:1][N:2]([CH3:6])[C:3](Cl)=[O:4].[OH:7][C:8]([C:10]([F:13])([F:12])[F:11])=[O:9].[F:14][C:15]1[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:16]=1[CH:22]([F:43])[CH:23]1[CH2:28][CH2:27][N:26]([C:29]2[N:34]=[C:33]3[CH2:35][NH:36][CH2:37][CH2:38][C:32]3=[N:31][C:30]=2[NH:39][CH:40]([CH3:42])[CH3:41])[CH2:25][CH2:24]1.C(N(CC)CC)C>C(Cl)Cl>[F:14][C:15]1[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:16]=1[CH:22]([F:43])[CH:23]1[CH2:28][CH2:27][N:26]([C:29]2[N:34]=[C:33]3[CH2:35][N:36]([C:3]([N:2]([CH3:6])[CH3:1])=[O:4])[CH2:37][CH2:38][C:32]3=[N:31][C:30]=2[NH:39][CH:40]([CH3:41])[CH3:42])[CH2:25][CH2:24]1.[C:8]([OH:9])([C:10]([F:13])([F:12])[F:11])=[O:7]

Participants

6

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 8471TriethylamineHCID 131734035HCID 131734035, compound

Product 2

HCID 6422Trifluoroacetic acidYield 467.7%HCID 118159294HCID 118159294, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dimethylcarbamic chloride (8.4 mg, 0.078 mmol) was added to a solution of 3-(4-((2,4-difluorophenyl)fluoromethyl)piperidin-1-yl)-N-isopropyl-5,6,7,8-tetrahydropyrido[3,4-b]pyrazin-2-amine TFA salt (20.8 mg, 0.039 mmol) and triethylamine (16 μL, 0.117 mmol) in DCM (390 μL) at rt. After 1 h, the mixture was purified by HPLC Method A to give the title compound as a TFA salt (20.8 mg, 88%) as a yellow film. 1H NMR (400 MHz, methanol-d4) δ ppm 1.31 (dd, J=6.6, 1.8 Hz, 6H), 1.40-1.48 (m, 1H), 1.58-1.78 (m, 2H), 1.95-2.03 (m, 1H), 2.03-2.18 (m, 1H), 2.71-2.88 (m, 4H), 2.90 (s, 6H), 3.42-3.52 (m, 2H), 3.54 (t, J=5.7 Hz, 2H), 4.07-4.16 (m, 1H), 4.22-4.27 (m, 2H), 5.53 (dd, J=46.5, 7.3 Hz, 1H), 6.97-7.08 (m, 2H), 7.47-7.55 (m, 1H); ESI-MS m/z [M+H]+ 491.4.

Workup

  1. customthe mixture was purified by HPLC Method A

Sources & evidence

ORD record
ord-b48c9d3fd0b04f458afa853a7684136d
Source dataset
uspto-grants-2015_11
Patent number
US09181249B2

Reaction notes

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