Diisopropylethylamine → HCID 46947169, compound

HRID 511199Notes

Reaction equation

HRID 511199 reaction equation
[Li+].[C:2]([C:6]1[CH:11]=[CH:10][C:9]([N:12]2[CH2:18][CH2:17][CH2:16][N:15]([CH2:19][CH2:20][CH2:21][C:22]([O-:24])=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+:50]([C:53]1[CH:58]=[CH:57][C:56]([NH:59][CH:60]2[CH2:65][CH2:64][NH:63][CH2:62][CH2:61]2)=[CH:55][C:54]=1[C:66]([F:69])([F:68])[F:67])([O-:52])=[O:51].C(N(C(C)C)CC)(C)C.[O-2].[Al+3].[O-2].[O-2].[Al+3]>O1CCCC1.CN(C)C=O>[C:2]([C:6]1[CH:11]=[CH:10][C:9]([N:12]2[CH2:18][CH2:17][CH2:16][N:15]([CH2:19][CH2:20][CH2:21][C:22]([N:63]3[CH2:64][CH2:65][CH:60]([NH:59][C:56]4[CH:57]=[CH:58][C:53]([N+:50]([O-:52])=[O:51])=[C:54]([C:66]([F:67])([F:68])[F:69])[CH:55]=4)[CH2:61][CH2:62]3)=[O:24])[CH2:14][CH2:13]2)=[CH:8][CH:7]=1)([CH3:3])([CH3:5])[CH3:4]

Participants

8

Reactant 5

HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 9989226AluminaHCID 58576078HCID 58576078, compoundHCID 66671805(4-Nitro-3-trifluoromethyl-phenyl)-piperidin-4-yl-amine hydrochloride

Product 1

HCID 46947169HCID 46947169, compoundYield 18%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-[4-(4-tert-butyl-phenyl)-[1,4]diazepan-1-yl]-butyric acid lithium salt (16 mg; 0.05 mmol, prepared in accordance with Example 162) 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 (5 mg; 0.009 mmol). The structure was confirmed using Protocol I-D. Calculated mass=590; observed mass=590; HPLC retention time=1.66 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-3aebe1686b4d4655b333381fb58c6b44
Source dataset
uspto-grants-2015_08
Patent number
US09096524B2

Reaction notes

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