Triethylamine → HCID 67059680, compound

HRID 1807756Notes

Reaction equation

HRID 1807756 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][C:3]=1[F:11].[CH2:12]([N:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(N(CC)CC)C.CCCP1(OP(CCC)(=O)OP(CCC)(=O)O1)=O>ClCCl>[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([N:22]2[CH2:23][CH2:24][N:19]([CH2:12][C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH2:20][CH2:21]2)=[O:8])=[CH:4][C:3]=1[F:11]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 99714-Amino-3-fluorobenzoic acidHCID 759941-BenzylpiperazineHCID 111923Propylphosphonic anhydride

Product 1

HCID 67059680HCID 67059680, compoundYield 84.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Amino-3-fluorobenzoic acid (28.4 mmol, 4.40 g), 1-benzylpiperazine (28.4 mmol, 4.93 mL, 5 g) and triethylamine (85 mmol, 11.86 mL, 8.61 g) were stirred in dichloromethane at room temperature. 1-Propanephosphonic acid cyclic anhydride (42.6 mmol, 25.2 mL, 27.1 g, 50% solution in ethyl acetate) was added and the reaction mixture stirred at room temperature for 1 hour. The reaction mixture was washed with saturated sodium bicarbonate solution and concentrated under reduced pressure to afford the title compound (7.51 g). MS (ESI) m/z 314.1 [M+H]+

Workup

  1. washThe reaction mixture was washed with saturated sodium bicarbonate solution
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d5ab62cfd06e45d88e451729534d2a48
Source dataset
uspto-grants-2013_01
Patent number
US08357679B2

Reaction notes

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