Diisopropylethylamine → HCID 58577021, compound

HRID 511168Notes

Reaction equation

HRID 511168 reaction equation
[Li+].[C:2]([C:6]1[CH:11]=[CH:10][C:9]([N:12]2[CH2:16][CH:15]3[CH2:17][N:18]([CH2:20][CH2:21][C:22]([O-])=[O:23])[CH2:19][CH:14]3[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]>CN(C)C=O.O1CCCC1>[C:2]([C:6]1[CH:7]=[CH:8][C:9]([N:12]2[CH2:16][CH:15]3[CH2:17][N:18]([CH2:20][CH2:21][C:22]([N:63]4[CH2:64][CH2:65][CH:60]([NH:59][C:56]5[CH:57]=[CH:58][C:53]([N+:50]([O-:52])=[O:51])=[C:54]([C:66]([F:67])([F:68])[F:69])[CH:55]=5)[CH2:61][CH2:62]4)=[O:23])[CH2:19][CH:14]3[CH2:13]2)=[CH:10][CH:11]=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 58576160HCID 58576160, compoundHCID 66671805(4-Nitro-3-trifluoromethyl-phenyl)-piperidin-4-yl-amine hydrochloride

Product 1

HCID 58577021HCID 58577021, compoundYield 24%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

3-[5-(4-tert-Butyl-phenyl)-hexahydro-pyrrolo[3,4-c]pyrrol-2-yl]-propionic acid lithium salt (16 mg; 0.05 mmol, prepared in accordance with Example 127) 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 and (0.25 mL) 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 (7 mg; 0.012 mmol). The structure was confirmed using Protocol I-D. Calculated mass=588; observed mass=588; 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-266d3e7c627445d580339ec2462d23a3
Source dataset
uspto-grants-2015_08
Patent number
US09096524B2

Reaction notes

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