Triethylamine → (4-Amino-3-(trifluoromethoxy)phenyl)(4-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)benzyl)piperazin-1-yl)methanone

HRID 1807770Notes

Reaction equation

HRID 1807770 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][C:3]=1[O:11][C:12]([F:15])([F:14])[F:13].[F:16][C:17]([F:38])([F:37])[C:18]([C:24]1[CH:29]=[CH:28][C:27]([CH2:30][N:31]2[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]2)=[CH:26][CH:25]=1)([OH:23])[C:19]([F:22])([F:21])[F:20].C(N(CC)CC)C.CCCP1(OP(CCC)(=O)OP(CCC)(=O)O1)=O>ClCCl.C(=O)([O-])O.[Na+]>[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([N:34]2[CH2:35][CH2:36][N:31]([CH2:30][C:27]3[CH:28]=[CH:29][C:24]([C:18]([OH:23])([C:19]([F:20])([F:21])[F:22])[C:17]([F:38])([F:16])[F:37])=[CH:25][CH:26]=3)[CH2:32][CH2:33]2)=[O:8])=[CH:4][C:3]=1[O:11][C:12]([F:15])([F:14])[F:13]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 111923Propylphosphonic anhydrideHCID 27359514-amino-3-(trifluoromethoxy)benzoic AcidHCID 866385661,1,1,3,3,3-Hexafluoro-2-(4-(piperazin-1-ylmethyl)phenyl)propan-2-ol

Product 1

HCID 59175861(4-Amino-3-(trifluoromethoxy)phenyl)(4-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)benzyl)piperazin-1-yl)methanoneYield 113%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

4-Amino-3-(trifluoromethoxy)benzoic acid (2.045 mmol, 0.452 g), 1,1,1,3,3,3-hexafluoro-2-(4-(piperazin-1-ylmethyl)phenyl)propan-2-ol (2.045 mmol, 0.700 g) and triethylamine (6.14 mmol, 0.853 mL, 0,621 g) were combined and stirred at room temperature in dichloromethane (5 mL). 1-Propanephosphonic acid cyclic anhydride (3.07 mmol, 1.826 mL, 1.952 g; 50% solution in ethyl acetate) was added and the reaction stirred for 1 hour. The reaction mixture was diluted with dichloromethane and saturated sodium hydrogen carbonate solution and the layers separated. The organic layer was dried over magnesium sulfate and concentrated under vacuum to afford the title compound (1.26 g). MS (ESI) m/z 546.5 [M+H]+

Workup

  1. customthe layers separated
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-00a5a4fbbc8f43c98d9f1f45741fe9b4
Source dataset
uspto-grants-2013_01
Patent number
US08357679B2

Reaction notes

Loading…