Triethylamine → HCID 86670929, compound

HRID 515268Notes

Reaction equation

HRID 515268 reaction equation
[NH2:1][C:2]1[CH:30]=[CH:29][C:5]([O:6][CH:7]2[CH2:11][CH2:10][N:9]([CH2:12][C:13]3[CH:18]=[CH:17][C:16]([C:19]([OH:28])([C:24]([F:27])([F:26])[F:25])[C:20]([F:23])([F:22])[F:21])=[CH:15][CH:14]=3)[CH2:8]2)=[CH:4][CH:3]=1.[C:31](Cl)(=O)[O:32]C1C=CC([N+]([O-])=O)=CC=1.[CH:44]1([CH2:47][NH2:48])[CH2:46][CH2:45]1.C(N(CC)CC)C>O1CCCC1.ClCCl>[CH:44]1([CH2:47][NH:48][C:31]([NH:1][C:2]2[CH:3]=[CH:4][C:5]([O:6][CH:7]3[CH2:11][CH2:10][N:9]([CH2:12][C:13]4[CH:14]=[CH:15][C:16]([C:19]([OH:28])([C:20]([F:21])([F:22])[F:23])[C:24]([F:27])([F:25])[F:26])=[CH:17][CH:18]=4)[CH2:8]3)=[CH:29][CH:30]=2)=[O:32])[CH2:46][CH2:45]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 75646CyclopropanemethanamineHCID 821294-Nitrophenyl chloroformateHCID 86670930HCID 86670930, compound

Product 1

HCID 86670929HCID 86670929, compoundYield 16.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-(4-((3-(4-aminophenoxy)pyrrolidin-1-yl)methyl)phenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol (0.345 mmol, 150 mg) and 4-nitrophenyl carbonochloridate (0.345 mmol, 69.6 mg) in tetrahydrofuran (5 mL) was stirred at room temperature for 30 minutes. Cyclopropylmethanamine (0.691 mmol, 49.1 mg) was added, followed by triethylamine (0.691 mmol, 0.096 mL, 69.9 mg) and the reaction stirred at room temperature overnight. The reaction mixture was diluted with dichloromethane/saturated sodium bicarbonate solution and filtered through a hydrophobic frit. The organic layer was concentrated under vacuum. The residue was purified by prep-HPLC (acidic conditions) and SCX chromatography to give title compound (30 mg).

Workup

  1. filtrationfiltered through a hydrophobic frit
  2. concentrationThe organic layer was concentrated under vacuum
  3. customThe residue was purified by prep-HPLC (acidic conditions) and SCX chromatography

Sources & evidence

ORD record
ord-682f73754431431ab3399cbf076aedba
Source dataset
uspto-grants-2015_08
Patent number
US09108939B2

Reaction notes

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