Diisopropylethylamine → HCID 58577133, compound

HRID 511189Notes

Reaction equation

HRID 511189 reaction equation
[Li+].[F:2][C:3]([F:23])([F:22])[C:4]1[CH:5]=[CH:6][C:7]([N:10]2[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][CH2:18][C:19]([O-:21])=O)[CH2:12][CH2:11]2)=[N:8][CH:9]=1.F[P-](F)(F)(F)(F)F.CN(C)C(ON1C2C=CC=CC=2N=N1)=[N+](C)C.Cl.[N+:49]([C:52]1[CH:57]=[CH:56][C:55]([NH:58][CH:59]2[CH2:64][CH2:63][NH:62][CH2:61][CH2:60]2)=[CH:54][C:53]=1[C:65]([F:68])([F:67])[F:66])([O-:51])=[O:50].C(N(C(C)C)CC)(C)C.[O-2].[Al+3].[O-2].[O-2].[Al+3]>O1CCCC1.CN(C)C=O>[N+:49]([C:52]1[CH:57]=[CH:56][C:55]([NH:58][CH:59]2[CH2:60][CH2:61][N:62]([C:19](=[O:21])[CH2:18][CH2:17][CH2:16][N:13]3[CH2:12][CH2:11][N:10]([C:7]4[CH:6]=[CH:5][C:4]([C:3]([F:2])([F:23])[F:22])=[CH:9][N:8]=4)[CH2:15][CH2:14]3)[CH2:63][CH2:64]2)=[CH:54][C:53]=1[C:65]([F:68])([F:66])[F:67])([O-:51])=[O:50]

Participants

8

Reactant 5

HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 9989226AluminaHCID 58576150HCID 58576150, compoundHCID 66671805(4-Nitro-3-trifluoromethyl-phenyl)-piperidin-4-yl-amine hydrochloride

Product 1

HCID 58577133HCID 58577133, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-[4-(5-trifluoromethyl-pyridin-2-yl)-piperazin-1-yl]-butyric acid lithium salt (16 mg; 0.05 mmol, prepared in accordance with Example 150) in tetrahydrofuran (0.5 mL) is added tetramethyl-O-(1H-benzotriazol-1-yl)uronium hexafluorophosphate (19 mg; 0.05 mmol) in dimethylformamide (0.25 mL). A solution of (4-nitro-3-trifluoromethyl-phenyl)-piperidin-4-yl-amine hydrochloride (16 mg; 0.05 mmol, prepared in accordance with Example 8) in dimethylformamide (0.25 mL) and diisopropylethyl amine (25 μL; 0.15 mmol) are then added and the reaction is stirred. After 3 hours at room temperature, aluminium oxide (90 active basic) is added and stiffing is continued for 40 minutes. The solids are removed by filtration and the filtrate is concentrated under high vacuum. The obtained residue is purified by preparative HPLC to afford the desired compound (18 mg; 0.031 mmol). The structure was confirmed using Protocol I-D. Calculated mass=588; observed mass=589; HPLC retention time=1.50 min.

Workup

  1. waitstiffing is continued for 40 minutes
  2. customThe solids are removed by filtration
  3. concentrationthe filtrate is concentrated under high vacuum
  4. customThe obtained residue is purified by preparative HPLC

Sources & evidence

ORD record
ord-a9e560a2ece04772973c2dcd686a8526
Source dataset
uspto-grants-2015_08
Patent number
US09096524B2

Reaction notes

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