1,4-Dioxane → HCID 86670986, compound

HRID 515358Notes

Reaction equation

HRID 515358 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)=[C:4]([F:33])[CH:3]=1.[N:34]1[CH:39]=[CH:38][C:37]([NH:40][C:41](=O)[O:42]C2C=CC=CC=2)=[CH:36][CH:35]=1.O1CCOCC1>O1CCCC1>[F:33][C:4]1[CH:3]=[C:2]([NH:1][C:41]([NH:40][C:37]2[CH:38]=[CH:39][N:34]=[CH:35][CH:36]=2)=[O:42])[CH:7]=[CH:6][C:5]=1[N:8]([CH:9]1[CH2:14][CH2:13][N:12]([CH2:15][C:16]2[CH:17]=[CH:18][C:19]([C:22]([OH:31])([C:23]([F:24])([F:25])[F:26])[C:27]([F:30])([F:28])[F:29])=[CH:20][CH:21]=2)[CH2:11][CH2:10]1)[CH3:32]

Participants

5

Reactant 3

HCID 312751,4-DioxaneHCID 11401617Carbamic acid, 4-pyridinyl-, phenyl esterHCID 86670985HCID 86670985, compound

Product 1

HCID 86670986HCID 86670986, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(4-((4-((4-Amino-2-fluorophenyl)(methyl)amino)piperidin-1-yl)methyl)-phenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol (0.209 mmol, 100 mg) and phenyl pyridin-4-ylcarbamate (0.313 mmol, 67.0 mg) were combined in tetrahydrofuran (1 mL) and dioxane (1 mL) and heated to 80° C. overnight. The reaction mixture was concentrated under vacuum. The residue was purified by prep-HPLC (acidic conditions) and SCX chromatography to afford title compound (83.9 mg). MS (ESI) m/z 600.2 [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-94ff80e7f80a40038cab097b96698da6
Source dataset
uspto-grants-2015_08
Patent number
US09108939B2

Reaction notes

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