Triethylamine → HCID 59175883, compound

HRID 1807768Notes

Reaction equation

HRID 1807768 reaction equation
[NH2:1][C:2]1[C:10]([F:11])=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][C:3]=1[F:12].[F:13][C:14]([F:35])([F:34])[C:15]([C:21]1[CH:26]=[CH:25][C:24]([CH2:27][N:28]2[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]2)=[CH:23][CH:22]=1)([OH:20])[C:16]([F:19])([F:18])[F:17].C(N(CC)CC)C.CCCP1(OP(CCC)(=O)OP(CCC)(=O)O1)=O.C(=O)([O-])O.[Na+]>ClCCl>[NH2:1][C:2]1[C:3]([F:12])=[CH:4][C:5]([C:6]([N:31]2[CH2:32][CH2:33][N:28]([CH2:27][C:24]3[CH:25]=[CH:26][C:21]([C:15]([OH:20])([C:16]([F:17])([F:18])[F:19])[C:14]([F:35])([F:13])[F:34])=[CH:22][CH:23]=3)[CH2:29][CH2:30]2)=[O:8])=[CH:9][C:10]=1[F:11]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 111923Propylphosphonic anhydrideHCID 2821334-amino-3,5-difluorobenzoic acidHCID 516892Sodium BicarbonateHCID 866385661,1,1,3,3,3-Hexafluoro-2-(4-(piperazin-1-ylmethyl)phenyl)propan-2-ol

Product 1

HCID 59175883HCID 59175883, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Amino-3,5-difluorobenzoic acid (1.899 mmol, 329 mg), 1,1,1,3,3,3-hexafluoro-2-(4-(piperazin-1-ylmethyl)phenyl)propan-2-ol (1.899 mmol, 650 mg) and triethylamine (5.70 mmol, 0.792 mL, 576 mg) were combined and stirred at room temperature in dichloromethane (5 mL). 1-Propanephosphonic acid cyclic anhydride (2.85 mmol, 1.696 mL, 1813 mg; 50% solution in ethyl acetate) was added and the reaction stirred for 2 hours. Saturated sodium hydrogen carbonate solution was added to the reaction mixture and the layers separated. The organic layer was dried over magnesium sulfate and concentrated under vacuum to afford the title compound (340 mg) as a pale pink solid. MS (ESI) m/z 498.7 [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-cdbe0c107ac8426e88dd4d1af0b3c175
Source dataset
uspto-grants-2013_01
Patent number
US08357679B2

Reaction notes

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