Dimethylcarbamoyl Chloride → Trifluoroacetic acid

HRID 713332Notes

Reaction equation

HRID 713332 reaction equation
[OH:1][C:2]([C:4]([F:7])([F:6])[F:5])=[O:3].[C:8]([NH:12][C:13]1[N:14]=[C:15]2[CH2:37][CH2:36][NH:35][CH2:34][C:16]2=[N:17][C:18]=1[N:19]1[CH2:24][CH2:23][CH:22]([O:25][C:26]2[CH:31]=[CH:30][C:29]([F:32])=[CH:28][C:27]=2[F:33])[CH2:21][CH2:20]1)([CH3:11])([CH3:10])[CH3:9].[CH3:38][N:39]([CH3:43])[C:40](Cl)=[O:41].CCN(C(C)C)C(C)C>C(Cl)Cl.CN(C=O)C>[C:8]([NH:12][C:13]1[N:14]=[C:15]2[CH2:37][CH2:36][N:35]([C:40]([N:39]([CH3:43])[CH3:38])=[O:41])[CH2:34][C:16]2=[N:17][C:18]=1[N:19]1[CH2:20][CH2:21][CH:22]([O:25][C:26]2[CH:31]=[CH:30][C:29]([F:32])=[CH:28][C:27]=2[F:33])[CH2:23][CH2:24]1)([CH3:11])([CH3:9])[CH3:10].[C:2]([OH:3])([C:4]([F:7])([F:6])[F:5])=[O:1]

Participants

7

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 81531DiisopropylethylamineHCID 131734039HCID 131734039, compound

Product 2

HCID 6422Trifluoroacetic acidYield 292.3%HCID 118159246HCID 118159246, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of N-(tert-butyl)-3-(4-(2,4-difluorophenoxyl)piperidin-1-yl)-5,6,7,8-tetrahydropyrido[3,4-b]pyrazin-2-amine TFA salt (16 mg, 0.030 mmol), dimethylcarbamic chloride (3.2 mg, 0.030 mmol), and DIPEA (5.3 μL, 0.030 mmol) in DCM (151 μL) was stirred at room temperature overnight. The crude reaction mixture was diluted in DMF, filtered through a hydrophilic PTFE 0.45 μm filter (Millipore® Millex-LCR), and purified via HPLC Method A to give the title compound as a TFA salt (10 mg) as a clear oil. 1H NMR (400 MHz, methanol-d4) δ ppm 1.48 (s, 9H), 1.87-1.97 (m, 2H), 2.07-2.17 (m, 2H), 2.82 (t, J=5.9 Hz, 2H), 2.90 (s, 6H), 2.95 (ddd, J=12.2, 8.5, 3.3 Hz, 2H), 3.29-3.35 (m, 2H), 3.53 (t, J=5.8 Hz, 2H), 4.25 (s, 2H), 4.46 (tt, J=7.5, 3.8 Hz, 1H), 6.84-6.91 (m, 1H), 6.99 (ddd, J=11.4, 8.6, 3.0 Hz, 1H), 7.18 (td, J=9.3, 5.4 Hz, 1H); ESI-MS m/z [M+H]+489.4.

Workup

  1. customThe crude reaction mixture
  2. filtrationfiltered through a hydrophilic PTFE 0.45 μm
  3. filtrationfilter (Millipore® Millex-LCR)
  4. custompurified via HPLC Method A

Sources & evidence

ORD record
ord-d68eb788797a4627b4fceea79e75f714
Source dataset
uspto-grants-2015_11
Patent number
US09181249B2

Reaction notes

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