2,2,2-Trifluoroethylamine hydrochloride → HCID 57794495, compound

HRID 2099305Notes

Reaction equation

HRID 2099305 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([NH:21][C:22]2[CH:27]=[CH:26][N:25]=[CH:24][N:23]=2)[C:5]2[N:10]([CH2:11][CH2:12][O:13][CH2:14][C:15]([F:18])([F:17])[F:16])[N:9]=[C:8]([CH2:19]Cl)[C:6]=2[N:7]=1.Cl.[F:29][C:30]([F:34])([F:33])[CH2:31][NH2:32].C(N(CC)C(C)C)(C)C>[Br-].C([N+](CC)(CC)CC)C.[I-].C([N+](CC)(CC)CC)C.CS(C)=O>[F:16][C:15]([F:18])([F:17])[CH2:14][O:13][CH2:12][CH2:11][N:10]1[C:5]2[C:4]([NH:21][C:22]3[CH:27]=[CH:26][N:25]=[CH:24][N:23]=3)=[N:3][C:2]([Cl:1])=[N:7][C:6]=2[C:8]([CH2:19][NH:32][CH2:31][C:30]([F:34])([F:33])[F:29])=[N:9]1

Participants

7

Reactant 3

HCID 97722,2,2-Trifluoroethylamine hydrochloride2×HCID 81531Diisopropylethylamine2×HCID 86624993HCID 86624993, compound

Product 1

HCID 57794495HCID 57794495, compound

Reagents, catalysts & solvents 3

HCID 6225Tetraethylammonium IodideCatalystHCID 6285Tetraethylammonium BromideCatalystHCID 679Dimethyl SulfoxideSolvent

Procedure

5-Chloro-3-(chloromethyl)-N-pyrimidin-4-yl-1-[2-(2,2,2-trifluoroethoxy)ethyl]-1H-pyrazolo[4,3-d]pyrimidin-7-amine (610 mg, 1.5 mmol), trifluoroethylamine hydrochloride (390 mg, 2.9 mmol) and N,N-diisopropylethylamine (410 mg, 3.2 mmol) along with tetraethylammonium bromide (1 mg) and tetraethylammonium iodide were mixed in dimethyl sulfoxide (10 ml) in a reaction vial. The reaction mixture was stirred for two days at room temperature and a second quantity of trifluoroethylamine hydrochloride (390 mg, 2.9 mmol) and N,N-diisopropyl-ethylamine (410 mg, 3.2 mmol) were added and the reaction allowed to proceed for another two days. The reaction mixture was partitioned between ethyl acetate (70 mLs) and water (2×25 mLs) and the organic layer dried (Na2SO4) and concentrated to an oil that solidified on standing. This intermediate was used without further purification. MS ES+ [MH]+m/z (relative intensity): 485.1 (100), 486.1 (10), 487.1 (20).

Workup

  1. waitto proceed for another two days
  2. customThe reaction mixture was partitioned between ethyl acetate (70 mLs) and water (2×25 mLs)
  3. dry with materialthe organic layer dried (Na2SO4)
  4. concentrationconcentrated to an oil that
  5. customThis intermediate was used without further purification

Sources & evidence

ORD record
ord-6b20041fe7974037b081439e620c515f
Source dataset
uspto-grants-2009_08
Patent number
US07569572B2

Reaction notes

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