Ethylamine → N-ethyl-2-(4-((4-((2,4,6-trifluorobenzyl)amino)pyrimidin-2-yl)amino)-1H-pyrazol-1-yl)acetamide

HRID 929926Notes

Reaction equation

HRID 929926 reaction equation
[F:1][C:2]1[CH:25]=[C:24]([F:26])[CH:23]=[C:22]([F:27])[C:3]=1[CH2:4][NH:5][C:6]1[CH:11]=[CH:10][N:9]=[C:8]([NH:12][C:13]2[CH:14]=[N:15][N:16]([CH2:18][C:19](O)=[O:20])[CH:17]=2)[N:7]=1.[CH3:28][CH2:29][N:30](C(C)C)C(C)C.CN(C(F)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N)C>O1CCOCC1.O>[CH2:29]([NH:30][C:19](=[O:20])[CH2:18][N:16]1[CH:17]=[C:13]([NH:12][C:8]2[N:7]=[C:6]([NH:5][CH2:4][C:3]3[C:22]([F:27])=[CH:23][C:24]([F:26])=[CH:25][C:2]=3[F:1])[CH:11]=[CH:10][N:9]=2)[CH:14]=[N:15]1)[CH3:28]

Participants

7

Reactant 4

HCID 6341EthylamineHCID 81531DiisopropylethylamineHCID 2774761Tetramethylfluoroformamidinium hexafluorophosphateHCID 900240572-(4-((4-((2,4,6-trifluorobenzyl)amino)pyrimidin-2-yl)amino)-1H-pyrazol-1-yl)acetic acid

Product 1

HCID 72706528N-ethyl-2-(4-((4-((2,4,6-trifluorobenzyl)amino)pyrimidin-2-yl)amino)-1H-pyrazol-1-yl)acetamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 2-(4-((4-((2,4,6-trifluorobenzyl)amino)pyrimidin-2-yl)amino)-1H-pyrazol-1-yl)acetic acid I-2 (80 mg, 0.21 mmol, prepared by Procedure B), DIPEA (187 μL, 1.06 mmol) and TFFH (61 mg, 0.23 mmol) in dioxane (4 mL) was stirred for 10 min at room temperature. Ethylamine (2M in THF, 529 μL, 1.06 mmol) was added and the reaction was stirred for 2 h, then diluted with water and extracted with DCM. The organic layer was concentrated in vacuo and purified by prep. HPLC to afford N-ethyl-2-(4-((4-((2,4,6-trifluorobenzyl)amino)pyrimidin-2-yl)amino)-1H-pyrazol-1-yl)acetamide I-6 (8.8 mg, 0.02 mmol). LC-MS (Method B), RT=5.23 min. (ES+) 406.

Workup

  1. stirringthe reaction was stirred for 2 h
  2. extractionextracted with DCM
  3. concentrationThe organic layer was concentrated in vacuo
  4. custompurified by prep

Sources & evidence

ORD record
ord-752758e9f22a4f40b406503892fadda3
Source dataset
uspto-grants-2016_03
Patent number
US09296725B2

Reaction notes

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