Triethylamine → HCID 86670989, compound

HRID 515361Notes

Reaction equation

HRID 515361 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:29]=[CH:30][CH:31]=1)[O:5][CH:6]1[CH2:11][CH2:10][N:9]([CH2:12][C:13]2[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]=2)[CH2:8][CH2:7]1.[C:32](Cl)(=O)[O:33]C1C=CC([N+]([O-])=O)=CC=1.C(N(CC)CC)C.[NH2:52][CH2:53][C:54]([CH3:57])([OH:56])[CH3:55]>ClCCl>[F:26][C:24]([F:27])([F:25])[C:19]([C:16]1[CH:15]=[CH:14][C:13]([CH2:12][N:9]2[CH2:10][CH2:11][CH:6]([O:5][C:4]3[CH:3]=[C:2]([NH:1][C:32]([NH:52][CH2:53][C:54]([OH:56])([CH3:57])[CH3:55])=[O:33])[CH:31]=[CH:30][CH:29]=3)[CH2:7][CH2:8]2)=[CH:18][CH:17]=1)([OH:28])[C:20]([F:21])([F:22])[F:23]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 821294-Nitrophenyl chloroformateHCID 951022-Propanol, 1-amino-2-methyl-HCID 86670988HCID 86670988, compound

Product 1

HCID 86670989HCID 86670989, compoundYield 47.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 2-(4-((4-(3-aminophenoxy)piperidin-1-yl)methyl)phenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol (1.115 mmol, 500 mg) in dichloromethane was added 4-nitrophenyl carbonochloridate (1.115 mmol, 225 mg) followed by triethylamine (1.115 mmol, 155 μl, 113 mg). The reaction was stirred for 30 minutes then 1-amino-2-methylpropan-2-ol (2.230 mmol, 199 mg) was added. The reaction was stirred for 2 hours then was chromatographed on silica (eluting with a gradient of dichloromethane to dichloromethane/methanol (8%)) to give the title compound (300 mg). MS (ESI) m/z 564.2 [M+H]+

Workup

  1. stirringThe reaction was stirred for 2 hours
  2. customthen was chromatographed on silica (
  3. washeluting with a gradient of dichloromethane to dichloromethane/methanol (8%))

Sources & evidence

ORD record
ord-09e091c13534402786e882bf7f1d03bd
Source dataset
uspto-grants-2015_08
Patent number
US09108939B2

Reaction notes

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