Dimethylcarbamoyl Chloride → Trifluoroacetic acid

HRID 713319Notes

Reaction equation

HRID 713319 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:30]=[C:31]3[CH2:42][CH2:41][NH:40][CH2:39][C:32]3=[N:33][C:34]=2[NH:35][CH:36]([CH3:38])[CH3:37])[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:30]=[C:31]3[CH2:42][CH2:41][N:40]([C:3]([N:2]([CH3:6])[CH3:1])=[O:4])[CH2:39][C:32]3=[N:33][C:34]=2[NH:35][CH:36]([CH3:38])[CH3:37])[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 131734036HCID 131734036, compound

Product 2

HCID 6422Trifluoroacetic acidYield 464.5%HCID 118159153HCID 118159153, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dimethylcarbamic chloride (5.8 mg, 0.054 mmol) was added to a solution of 2-(4-((2,4-difluorophenyl)fluoromethyl)piperidin-1-yl)-N-isopropyl-5,6,7,8-tetrahydropyrido[3,4-b]pyrazin-3-amine TFA salt (14.3 mg, 0.027 mmol) and triethylamine (11 μL, 0.080 mmol) in DCM (270 μL) at rt. After 1 h, the mixture was purified by HPLC Method A to give the title compound as a TFA salt (14.3 mg, 88%) as a yellow film. 1H NMR (400 MHz, methanol-d4) δ ppm 1.29 (dd, J=6.4, 1.9 Hz, 6H), 1.40-1.49 (m, 1H), 1.55-1.77 (m, 2H), 2.01 (d, J=13.1 Hz, 2H), 2.70-2.84 (m, 4H), 2.87-2.94 (m, 6H), 3.40-3.52 (m, 2H), 3.53-3.57 (m, 2H), 4.11 (quin, J=6.4 Hz, 1H) 4.29 (s, 2H) 5.53 (dd, J=46.2, 7.3 Hz, 1H), 6.97-7.09 (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-b79bb3a9743044ebbdecbaebd2f6d25d
Source dataset
uspto-grants-2015_11
Patent number
US09181249B2

Reaction notes

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