Diisopropylethylamine → HCID 58575984, compound

HRID 511169Notes

Reaction equation

HRID 511169 reaction equation
[Li+].[C:2]([C:6]1[CH:11]=[CH:10][C:9]([N:12]2[CH2:17][CH2:16][N:15]([CH2:18][CH:19]([CH3:23])[C:20]([O-:22])=O)[CH2:14][CH2:13]2)=[CH:8][CH:7]=1)([CH3:5])([CH3:4])[CH3:3].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]>CN(C)C=O.O1CCCC1>[C:2]([C:6]1[CH:11]=[CH:10][C:9]([N:12]2[CH2:17][CH2:16][N:15]([CH2:18][CH:19]([CH3:23])[C:20]([N:62]3[CH2:63][CH2:64][CH:59]([NH:58][C:55]4[CH:56]=[CH:57][C:52]([N+:49]([O-:51])=[O:50])=[C:53]([C:65]([F:66])([F:67])[F:68])[CH:54]=4)[CH2:60][CH2:61]3)=[O:22])[CH2:14][CH2:13]2)=[CH:8][CH:7]=1)([CH3:3])([CH3:4])[CH3:5]

Participants

8

Reactant 5

HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 9989226AluminaHCID 58576051HCID 58576051, compoundHCID 66671805(4-Nitro-3-trifluoromethyl-phenyl)-piperidin-4-yl-amine hydrochloride

Product 1

HCID 58575984HCID 58575984, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

3-[4-(4-tert-Butyl-phenyl)-piperazin-1-yl]-2-methyl-propionic acid lithium salt (15 mg; 0.05 mmol, prepared in accordance with Example 129) and tetramethyl-O-(1H-benzotriazol-1-yl)uronium hexafluorophosphate (19 mg; 0.05 mmol) are diluted in a 2 to 1 mixture of dimethylformamide and tetrahydrofuran (0.75 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 added and the reaction is then stirred. After 4 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 (15 mg; 0.025 mmol). The structure was confirmed using Protocol I-D. Calculated mass=576; observed mass=576; HPLC retention time=1.61 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-edada636ab3f43018de47c3686ad8296
Source dataset
uspto-grants-2015_08
Patent number
US09096524B2

Reaction notes

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