Triethylamine → HCID 86670945, compound

HRID 515291Notes

Reaction equation

HRID 515291 reaction equation
[NH2:1][C:2]1[CH:31]=[CH:30][C:5]([CH2:6][CH:7]2[CH2:12][CH2:11][N:10]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([C:20]([OH:29])([C:25]([F:28])([F:27])[F:26])[C:21]([F:24])([F:23])[F:22])=[CH:16][CH:15]=3)[CH2:9][CH2:8]2)=[CH:4][C:3]=1[F:32].[C:33](Cl)(=O)[O:34]C1C=CC([N+]([O-])=O)=CC=1.[CH3:46][C:47]([NH2:51])([CH3:50])[CH2:48][NH2:49].C(N(CC)CC)C>O1CCCC1>[NH2:51][C:47]([CH3:50])([CH3:46])[CH2:48][NH:49][C:33]([NH:1][C:2]1[CH:31]=[CH:30][C:5]([CH2:6][CH:7]2[CH2:12][CH2:11][N:10]([CH2:13][C:14]3[CH:15]=[CH:16][C:17]([C:20]([OH:29])([C:21]([F:22])([F:23])[F:24])[C:25]([F:28])([F:26])[F:27])=[CH:18][CH:19]=3)[CH2:9][CH2:8]2)=[CH:4][C:3]=1[F:32])=[O:34]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 131282-MethylpropylenediamineHCID 821294-Nitrophenyl chloroformateHCID 866709462-(4-((4-(4-Amino-3-fluorobenzyl)piperidin-1-yl)methyl)phenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol

Product 1

HCID 86670945HCID 86670945, compoundYield 9.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-(4-((4-(4-amino-3-fluorobenzyl)piperidin-1-yl)methyl)phenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol (0.861 mmol, 0.4 g) and 4-nitrophenyl carbonochloridate (0.861 mmol, 0.174 g) in tetrahydrofuran (5 mL) was stirred at room temperature for 30 minutes. 2-Methylpropane-1,2-diamine (1.723 mmol, 0.152 g) was added, followed by triethylamine (2.58 mmol, 0.360 mL, 0.261 g) and the reaction stirred at room temperature overnight. The reaction mixture was concentrated under vacuum. The residue was purified by prep-HPLC (acidic conditions) and SCX chromatography to afford the title compound (45.3 mg). MS (ESI) m/z 579.2 [M+H]+

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. customThe residue was purified by prep-HPLC (acidic conditions) and SCX chromatography

Sources & evidence

ORD record
ord-52facda606fd4f5db781a03230012b80
Source dataset
uspto-grants-2015_08
Patent number
US09108939B2

Reaction notes

Loading…