1,4-Dioxane → HCID 86670982, compound

HRID 515353Notes

Reaction equation

HRID 515353 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH3:32])[CH:9]2[CH2:14][CH2:13][N:12]([CH2:15][C:16]3[CH:21]=[CH:20][C:19]([C:22]([OH:31])([C:27]([F:30])([F:29])[F:28])[C:23]([F:26])([F:25])[F:24])=[CH:18][CH:17]=3)[CH2:11][CH2:10]2)=[CH:4][CH:3]=1.[N:33]1[CH:38]=[CH:37][C:36]([NH:39][C:40](=O)[O:41]C2C=CC=CC=2)=[CH:35][CH:34]=1.O1CCOCC1>O1CCCC1>[F:26][C:23]([F:24])([F:25])[C:22]([C:19]1[CH:20]=[CH:21][C:16]([CH2:15][N:12]2[CH2:11][CH2:10][CH:9]([N:8]([CH3:32])[C:5]3[CH:6]=[CH:7][C:2]([NH:1][C:40]([NH:39][C:36]4[CH:37]=[CH:38][N:33]=[CH:34][CH:35]=4)=[O:41])=[CH:3][CH:4]=3)[CH2:14][CH2:13]2)=[CH:17][CH:18]=1)([OH:31])[C:27]([F:30])([F:28])[F:29]

Participants

5

Reactant 3

HCID 312751,4-DioxaneHCID 11401617Carbamic acid, 4-pyridinyl-, phenyl esterHCID 86670981HCID 86670981, compound

Product 1

HCID 86670982HCID 86670982, compoundYield 29.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(4-((4-((4-Aminophenyl)(methyl)amino)piperidin-1-yl)methyl)phenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol (0.260 mmol, 120 mg) and phenyl pyridin-4-ylcarbamate (0.390 mmol, 84 mg) were combined in tetrahydrofuran (1 mL) and dioxane (1 mL) and heated to 100° C. overnight. The reaction mixture was concentrated under vacuum. The residue was purified by prep-HPLC (acidic conditions) and SCX chromatography to give the title compound (44.2 mg). MS (ESI) m/z 582.2 [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-d4046e68e63e4320be3943e1aa5fa47e
Source dataset
uspto-grants-2015_08
Patent number
US09108939B2

Reaction notes

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