Triethylamine → HCID 86670983, compound

HRID 515354Notes

Reaction equation

HRID 515354 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.[C:33](Cl)(=O)[O:34]C1C=CC([N+]([O-])=O)=CC=1.[O:46]1[CH2:51][CH2:50][CH:49]([NH2:52])[CH2:48][CH2:47]1.C(N(CC)CC)C>ClCCl>[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:33]([NH:52][CH:49]4[CH2:50][CH2:51][O:46][CH2:47][CH2:48]4)=[O:34])=[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

6

Reactant 4

HCID 8471TriethylamineHCID 821294-Nitrophenyl chloroformateHCID 4192234-AminotetrahydropyranHCID 86670981HCID 86670981, compound

Product 1

HCID 86670983HCID 86670983, compoundYield 41.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2-(4-((4-((4-aminophenyl)(methyl)amino)piperidin-1-yl)methyl)phenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol (0.303 mmol, 140 mg) and 4-nitrophenyl carbonochloridate (0.303 mmol, 61.2 mg) in dichloromethane (1 mL) was stirred at room temperature for 30 minutes. Tetrahydro-2H-pyran-4-amine (0.607 mmol, 61.4 mg) was added followed by triethylamine (0.910 mmol, 0.127 mL, 92 mg) and the reaction stirred at room temperature overnight. The reaction mixture was diluted with dichloromethane/saturated sodium bicarbonate solution and filtered through a hydrophobic frit. The organic layer was concentrated and the residue was purified by silica column chromatography (eluent: dichloromethane to 4% methanol in dichloromethane) to give the title compound (74.2 mg). MS (ESI) m/z 589.2 [M+H]+

Workup

  1. filtrationfiltered through a hydrophobic frit
  2. concentrationThe organic layer was concentrated
  3. customthe residue was purified by silica column chromatography (eluent: dichloromethane to 4% methanol in dichloromethane)

Sources & evidence

ORD record
ord-ee47743ca7d24359823d542ed6fb3d75
Source dataset
uspto-grants-2015_08
Patent number
US09108939B2

Reaction notes

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