Diisopropylethylamine → HCID 58576507, compound

HRID 511195Notes

Reaction equation

HRID 511195 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.C(N(C(C)C)CC)(C)C.Cl.[NH:58]1[CH2:63][CH2:62][CH:61]([NH:64][C:65]2[CH:72]=[CH:71][C:68]([C:69]#[N:70])=[C:67]([C:73]([F:76])([F:75])[F:74])[CH:66]=2)[CH2:60][CH2:59]1.[O-2].[Al+3].[O-2].[O-2].[Al+3]>O1CCCC1.CN(C)C=O>[C:2]([C:6]1[CH:7]=[CH:8][C:9]([N:12]2[CH2:13][CH2:14][N:15]([CH2:18][CH:19]([CH3:23])[C:20]([N:58]3[CH2:63][CH2:62][CH:61]([NH:64][C:65]4[CH:72]=[CH:71][C:68]([C:69]#[N:70])=[C:67]([C:73]([F:74])([F:75])[F:76])[CH:66]=4)[CH2:60][CH2:59]3)=[O:22])[CH2:16][CH2:17]2)=[CH:10][CH:11]=1)([CH3:5])([CH3:3])[CH3:4]

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 66671763HCID 66671763, compound

Product 1

HCID 58576507HCID 58576507, compoundYield 8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred suspension of 3-[4-(4-tert-butyl-phenyl)-piperazin-1-yl]-2-methyl-propionic acid lithium salt (16 mg; 0.05 mmol) in tetrahydrofuran (1.0 mL) is added tetramethyl-O-(1H-benzotriazol-1-yl)uronium hexafluorophosphate (19 mg; 0.05 mmol) in dimethylformaide (0.5 mL). 15 minutes later, diisopropylethyl amine (25 μL; 0.15 mmol) and a solution of 4-(piperidin-4-ylamino)-2-trifluoromethyl-benzonitrile hydrochloride (15 mg; 0.05 mmol, prepared in accordance with Example 155) in dimethylformamide (0.5 mL) are added. After 2 hours at room temperature, aluminium oxide (90 active basic) is added and stiffing is continued. 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 (2 mg; 0.004 mmol). The structure was confirmed using Protocol I-D. Calculated mass=556; observed mass=556; HPLC retention time=1.60 min.

Workup

  1. customThe solids are removed by filtration
  2. concentrationthe filtrate is concentrated under high vacuum
  3. customThe obtained residue is purified by preparative HPLC

Sources & evidence

ORD record
ord-7cef4c466b734c9694a7ff6e6030429c
Source dataset
uspto-grants-2015_08
Patent number
US09096524B2

Reaction notes

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