Isopropylamine → 1-(4-(4-(4-(1,1,1,3,3,3-Hexafluoro-2-hydroxypropan-2-yl)benzyl)piperazine-1-carbonyl)phenyl)-3-isopropylurea

HRID 1807715Notes

Reaction equation

HRID 1807715 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:10]2[CH2:15][CH2:14][N:13]([CH2:16][C:17]3[CH:22]=[CH:21][C:20]([C:23]([OH:32])([C:28]([F:31])([F:30])[F:29])[C:24]([F:27])([F:26])[F:25])=[CH:19][CH:18]=3)[CH2:12][CH2:11]2)=[O:9])=[CH:4][CH:3]=1.[CH:33]([N:36]([CH:39](C)C)CC)([CH3:35])[CH3:34].ClC(Cl)([O:45]C(=O)OC(Cl)(Cl)Cl)Cl.C(N)(C)C>ClCCl>[F:29][C:28]([F:31])([F:30])[C:23]([C:20]1[CH:19]=[CH:18][C:17]([CH2:16][N:13]2[CH2:14][CH2:15][N:10]([C:8]([C:5]3[CH:4]=[CH:3][C:2]([NH:1][C:39]([NH:36][CH:33]([CH3:35])[CH3:34])=[O:45])=[CH:7][CH:6]=3)=[O:9])[CH2:11][CH2:12]2)=[CH:22][CH:21]=1)([OH:32])[C:24]([F:25])([F:26])[F:27]

Participants

6

Reactant 4

HCID 6363IsopropylamineHCID 81531DiisopropylethylamineHCID 94429TriphosgeneHCID 86638547(4-Aminophenyl)(4-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)benzyl)piperazin-1-yl)methanone

Product 1

HCID 591758651-(4-(4-(4-(1,1,1,3,3,3-Hexafluoro-2-hydroxypropan-2-yl)benzyl)piperazine-1-carbonyl)phenyl)-3-isopropylureaYield 22.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(4-Aminophenyl)(4-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)benzyl)-piperazin-1-yl)methanone (0.217 mmol, 0.1 g) and diisopropylethylamine (0.737 mmol, 0.122 mL, 0.095 g) were stirred in dichloromethane at room temperature. Triphosgene (0.080 mmol, 0.024 g) was added and the reaction mixture stirred for 30 minutes. Isopropylamine (0.433 mmol, 0.037 mL, 0.026 g) was added and the reaction stirred for a further 30 minutes. The reaction mixture was concentrated under vacuum and purified by reverse phase acidic preparative HPLC to afford the title compound (10 mg).

Workup

  1. stirringthe reaction stirred for a further 30 minutes
  2. concentrationThe reaction mixture was concentrated under vacuum
  3. custompurified by reverse phase acidic preparative HPLC

Sources & evidence

ORD record
ord-9dc5c7a9f3aa453b9e740a8b835c936b
Source dataset
uspto-grants-2013_01
Patent number
US08357679B2

Reaction notes

Loading…