Triethylamine → HCID 86670971, compound

HRID 515340Notes

Reaction equation

HRID 515340 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH: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][C:3]=1[F:33].Cl[C:35](OC1C=CC([N+]([O-])=O)=CC=1)=[O:36].Cl.[O:48]1[CH2:52][CH2:51][C@H:50]([NH2:53])[CH2:49]1.C(N(CC)CC)C>O1CCCC1>[F:33][C:3]1[CH:4]=[C:5]([CH:8]([CH:9]2[CH2:10][CH2:11][N:12]([CH2:15][C:16]3[CH:17]=[CH:18][C:19]([C:22]([OH:31])([C:27]([F:30])([F:28])[F:29])[C:23]([F:24])([F:25])[F:26])=[CH:20][CH:21]=3)[CH2:13][CH2:14]2)[OH:32])[CH:6]=[CH:7][C:2]=1[NH:1][C:35]([NH:53][C@H:50]1[CH2:51][CH2:52][O:48][CH2:49]1)=[O:36]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 821294-Nitrophenyl chloroformateHCID 18664284(3S)-oxolan-3-amine hydrochlorideHCID 86670969HCID 86670969, compound

Product 1

HCID 86670971HCID 86670971, compoundYield 17.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(4-((4-((4-Amino-3-fluorophenyl)(hydroxy)methyl)piperidin-1-yl)methyl)phenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol (0.125 mmol, 60 mg) and 4-nitrophenyl chloroformate (0.125 mmol, 25.2 mg) were combined in tetrahydrofuran (2 mL) and the reaction stirred at room temperature for 1 hour. (S)-Tetrahydrofuran-3-amine hydrochloride (0.125 mmol, 15.43 mg) and triethylamine (0.500 mmol, 50.6 mg) were added and the mixture stirred at room temperature overnight. The mixture was concentrated under reduced pressure and the resulting residue purified by silica gel column chromatography (eluting with dichloromethane to 10% methanol/dichloromethane) to afford the title compound (13 mg). MS (ESI) m/z 594.7 [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 silica gel column chromatography (eluting with dichloromethane to 10% methanol/dichloromethane)

Sources & evidence

ORD record
ord-c902277b774a46f7bc7664b995d945f2
Source dataset
uspto-grants-2015_08
Patent number
US09108939B2

Reaction notes

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