Triethylamine → HCID 86670980, compound

HRID 515350Notes

Reaction equation

HRID 515350 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH:10]2[CH2:15][CH2:14][N:13]([CH2:16][C:17]3[CH:22]=[CH:21][C:20]([C:23]([OH:32])([C:28]([F:31])([F:30])[F:29])[C:24]([F:27])([F:26])[F:25])=[CH:19][CH:18]=3)[CH2:12][CH2:11]2)=[O:9])=[CH:4][CH:3]=1.Cl[C:34](OC1C=CC([N+]([O-])=O)=CC=1)=[O:35].[O:46]1[CH2:49][CH:48]([NH2:50])[CH2:47]1.C(N(CC)CC)C>O1CCCC1>[F:30][C:28]([F:31])([F:29])[C:23]([C:20]1[CH:21]=[CH:22][C:17]([CH2:16][N:13]2[CH2:14][CH2:15][CH:10]([C:8]([C:5]3[CH:6]=[CH:7][C:2]([NH:1][C:34]([NH:50][CH:48]4[CH2:49][O:46][CH2:47]4)=[O:35])=[CH:3][CH:4]=3)=[O:9])[CH2:11][CH2:12]2)=[CH:18][CH:19]=1)([OH:32])[C:24]([F:25])([F:26])[F:27]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 821294-Nitrophenyl chloroformateHCID 98339233-OxetanamineHCID 86670979HCID 86670979, compound

Product 1

HCID 86670980HCID 86670980, compoundYield 20.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(4-Aminophenyl)(1-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)benzyl)piperidin-4-yl)methanone (0.367 mmol, 169 mg) and 4-nitrophenyl chloroformate (0.367 mmol, 74.0 mg) were combined in tetrahydrofuran (2 mL) and stirred at room temperature for 1 hour. Oxetan-3-amine (0.734 mmol, 53.7 mg) and triethylamine (1.101 mmol, 111 mg) were added and the mixture stirred at room temperature overnight. The mixture was concentrated under reduced pressure and the resulting residue purified by basic HPLC to afford the title compound (43 mg). MS (ESI) m/z 560.2 [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 basic HPLC

Sources & evidence

ORD record
ord-f6c0cb7cd4b246c68537ebee99477e25
Source dataset
uspto-grants-2015_08
Patent number
US09108939B2

Reaction notes

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