Triethylamine → HCID 86670976, compound

HRID 515347Notes

Reaction equation

HRID 515347 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH:11]2[CH2:16][CH2:15][N:14]([CH2:17][C:18]3[CH:23]=[CH:22][C:21]([C:24]([OH:33])([C:29]([F:32])([F:31])[F:30])[C:25]([F:28])([F:27])[F:26])=[CH:20][CH:19]=3)[CH2:13][CH2:12]2)([OH:10])[CH3:9])=[CH:4][CH:3]=1.Cl[C:35](OC1C=CC([N+]([O-])=O)=CC=1)=[O:36].[NH2:47][CH2:48][C:49]([CH3:52])([OH:51])[CH3:50].[CH2:53](N(CC)CC)C>O1CCCC1>[F:28][C:25]([F:26])([F:27])[C:24]([C:21]1[CH:22]=[CH:23][C:18]([CH2:17][N:14]2[CH2:13][CH2:12][CH:11]([C:8]([C:5]3[CH:6]=[CH:7][C:2]([NH:1][C:35]([NH:47][CH2:48][C:49]([OH:51])([CH3:52])[CH3:50])=[O:36])=[CH:3][CH:4]=3)([O:10][CH3:53])[CH3:9])[CH2:16][CH2:15]2)=[CH:19][CH:20]=1)([OH:33])[C:29]([F:32])([F:30])[F:31]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 821294-Nitrophenyl chloroformateHCID 951022-Propanol, 1-amino-2-methyl-HCID 86670974HCID 86670974, compound

Product 1

HCID 86670976HCID 86670976, compoundYield 26.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(4-((4-(1-(4-Aminophenyl)-1-hydroxyethyl)piperidin-1-yl)methyl)phenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol (0.252 mmol, 120 mg) and 4-nitrophenyl chloroformate (0.252 mmol, 50.8 mg) were combined in tetrahydrofuran (2 mL) and the reaction stirred at room temperature for 1 hour. 1-Amino-2-methylpropan-2-ol (0.252 mmol, 22.45 mg) and triethylamine (0.756 mmol, 76 mg) were added and the mixture stirred at room temperature overnight. The mixture was concentrated under reduced pressure and the resulting residue purified by HPLC then treated with strong cation exchange column chromatography. The resulting product was purified by silica gel column chromatography (eluting with 2% to 15% methanol/dichloromethane) to afford the title compound (40 mg). MS (ESI) m/z 606.2 [M+H]+

Workup

  1. stirringthe mixture stirred at room temperature overnight
  2. concentrationThe mixture was concentrated under reduced pressure
  3. customthe resulting residue purified by HPLC
  4. additionthen treated with strong cation exchange column chromatography
  5. customThe resulting product was purified by silica gel column chromatography (eluting with 2% to 15% methanol/dichloromethane)

Sources & evidence

ORD record
ord-c907541664bd4ed4829df592d30ef7de
Source dataset
uspto-grants-2015_08
Patent number
US09108939B2

Reaction notes

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