Triethylamine → HCID 59175900, compound

HRID 1807800Notes

Reaction equation

HRID 1807800 reaction equation
[CH:1]1([CH2:4][NH:5][C:6](=[O:17])[CH2:7][C:8]2[CH:16]=[CH:15][C:11]([C:12]([O-:14])=O)=[CH:10][CH:9]=2)[CH2:3][CH2:2]1.[Na+].[F:19][C:20]([F:41])([F:40])[C:21]([C:27]1[CH:32]=[CH:31][C:30]([CH2:33][N:34]2[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]2)=[CH:29][CH:28]=1)([OH:26])[C:22]([F:25])([F:24])[F:23].C(N(CC)CC)C.CCCP1(OP(CCC)(=O)OP(CCC)(=O)O1)=O>ClCCl>[CH:1]1([CH2:4][NH:5][C:6](=[O:17])[CH2:7][C:8]2[CH:9]=[CH:10][C:11]([C:12]([N:37]3[CH2:38][CH2:39][N:34]([CH2:33][C:30]4[CH:31]=[CH:32][C:27]([C:21]([OH:26])([C:22]([F:23])([F:24])[F:25])[C:20]([F:41])([F:19])[F:40])=[CH:28][CH:29]=4)[CH2:35][CH2:36]3)=[O:14])=[CH:15][CH:16]=2)[CH2:2][CH2:3]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 111923Propylphosphonic anhydrideHCID 67059690Sodium 4-(2-(cyclopropylmethylamino)-2-oxoethyl)benzoateHCID 866385661,1,1,3,3,3-Hexafluoro-2-(4-(piperazin-1-ylmethyl)phenyl)propan-2-ol

Product 1

HCID 59175900HCID 59175900, compoundYield 1.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Sodium 4-(2-(cyclopropylmethylamino)-2-oxoethyl)benzoate (5.26 mmol, 1.342 g), 1,1,1,3,3,3-hexafluoro-2-(4-(piperazin-1-ylmethyl)phenyl)propan-2-ol (5.26 mmol, 1.800 g), and triethylamine (18.40 mmol, 2.56 mL, 1.862 g) were combined in dichloromethane (25 mL) and the reaction mixture stirred at room temperature for 15 minutes. 1-Propanephosphonic acid cyclic anhydride (7.89 mmol, 4.69 ml, 5.02 g; 50% solution in ethyl acetate) was added dropwise and the reaction mixture stirred at room temperature for 1 hour. The reaction mixture was washed with water, and the organic layer was separated and concentrated under vacuum to obtain crude product. The crude product was purified by SCX column chromatography, silica column chromatography (eluting with 90:10:1 dichloromethane/methanol/ammonia) and acidic preparative HPLC to afford the title compound (55.3 mg). MS (ESI) m/z 558.2 [M+H]+

Workup

  1. stirringthe reaction mixture stirred at room temperature for 1 hour
  2. washThe reaction mixture was washed with water
  3. customthe organic layer was separated
  4. concentrationconcentrated under vacuum
  5. customto obtain crude product
  6. customThe crude product was purified by SCX column chromatography, silica column chromatography (eluting with 90:10:1 dichloromethane/methanol/ammonia) and acidic preparative HPLC

Sources & evidence

ORD record
ord-31746dc027be4dfc9ec95a73625ff845
Source dataset
uspto-grants-2013_01
Patent number
US08357679B2

Reaction notes

Loading…