Triethylamine → HCID 57917659, compound

HRID 1878425Notes

Reaction equation

HRID 1878425 reaction equation
[CH:1]1([NH:5][C:6](=[O:20])[C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([CH2:13][N:14]3[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]3)[CH:8]=2)[CH2:4][CH2:3][CH2:2]1.[NH2:21][C:22]1[CH:30]=[CH:29][C:25]([C:26](O)=[O:27])=[CH:24][C:23]=1[F:31].C(N(CC)CC)C.CCCP1(OP(CCC)(=O)OP(CCC)(=O)O1)=O>ClCCl.C(OCC)(=O)C.C(=O)([O-])O.[Na+]>[NH2:21][C:22]1[CH:30]=[CH:29][C:25]([C:26]([N:17]2[CH2:16][CH2:15][N:14]([CH2:13][C:9]3[CH:8]=[C:7]([CH:12]=[CH:11][CH:10]=3)[C:6]([NH:5][CH:1]3[CH2:2][CH2:3][CH2:4]3)=[O:20])[CH2:19][CH2:18]2)=[O:27])=[CH:24][C:23]=1[F:31]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 99714-Amino-3-fluorobenzoic acidHCID 111923Propylphosphonic anhydrideHCID 57917592HCID 57917592, compound

Product 1

HCID 57917659HCID 57917659, compoundYield 66.6%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 86584982Sodium bicarbonate ethyl acetateSolvent

Procedure

To a solution of N-cyclobutyl-3-(piperazin-1-ylmethyl)benzamide (8.78 mmol, 2.4 g), 4-amino-3-fluorobenzoic acid (8.78 mmol, 1.362 g) and triethylamine (26.3 mmol, 3.67 mL, 2.67 g) in dichloromethane (50 mL) was added 1-propanephosphonic acid cyclic anhydride (13.17 mmol, 7.84 mL, 8.38 g, 50% solution in ethyl acetate). The reaction was stirred for 1 hour then was diluted with ethyl acetate/sodium hydrogen carbonate (aqueous). The organic layer was separated, dried (magnesium sulfate) and concentrated under reduced pressure to give the title compound (2.4 g).

Workup

  1. customThe organic layer was separated
  2. dry with materialdried (magnesium sulfate)
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-25fd4cfa5d2c4162ba2259bef6597ed2
Source dataset
uspto-grants-2012_11
Patent number
US08314091B2

Reaction notes

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