Triethylamine → 3-((4-(4-Amino-3-chloro-2-fluorobenzoyl)piperazin-1-yl)methyl)-N-tert-butylbenzamide

HRID 1878367

Reaction equation

HRID 1878367 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[C:4]([F:11])[C:3]=1[Cl:12].[C:13]([NH:17][C:18](=[O:32])[C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([CH2:25][N:26]2[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)[CH:20]=1)([CH3:16])([CH3:15])[CH3:14].C(N(CC)CC)C.CCCP1(OP(CCC)(=O)OP(CCC)(=O)O1)=O>ClCCl.C(OCC)(=O)C>[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([N:29]2[CH2:28][CH2:27][N:26]([CH2:25][C:21]3[CH:20]=[C:19]([CH:24]=[CH:23][CH:22]=3)[C:18]([NH:17][C:13]([CH3:15])([CH3:16])[CH3:14])=[O:32])[CH2:31][CH2:30]2)=[O:8])=[C:4]([F:11])[C:3]=1[Cl:12]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 111923Propylphosphonic anhydrideHCID 27627744-Amino-3-chloro-2-fluorobenzoic acidHCID 66877987N-tert-butyl-3-(piperazin-1-ylmethyl)benzamide

Product 1

HCID 579176553-((4-(4-Amino-3-chloro-2-fluorobenzoyl)piperazin-1-yl)methyl)-N-tert-butylbenzamideYield 46%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 4-amino-3-chloro-2-fluorobenzoic acid (0.754 mmol, 143 mg), N-tert-butyl-3-(piperazin-1-ylmethyl)benzamide (0.754 mmol, 208 mg) and triethylamine (3.02 mmol, 0.421 ml, 305 mg) in dichloromethane (8 mL) was added 1-propanephosphonic acid cyclic anhydride (1.886 mmol, 1.117 mL, 1200 mg, 50% solution in ethyl acetate). After 2 hours stirring, ethyl acetate was added. The organic solution was washed with saturated sodium hydrogen carbonate, water, and saturated sodium chloride. The organic phase was dried with sodium sulfate, filtered and concentrated. The residue was purified by silica chromatography to yield the title compound (155 mg).

Workup

  1. washThe organic solution was washed with saturated sodium hydrogen carbonate, water, and saturated sodium chloride
  2. dry with materialThe organic phase was dried with sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by silica chromatography

Sources & evidence

ORD record
ord-ef4b4b8a7b544ab182341076e62cfe74
Source dataset
uspto-grants-2012_11
Patent number
US08314091B2

Linked notes

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