Triethylamine → HCID 57917707, compound

HRID 1878358Notes

Reaction equation

HRID 1878358 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][C:3]=1[CH3:11].[C:12]([NH:16][C:17](=[O:31])[C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([CH2:24][N:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)[CH:19]=1)([CH3:15])([CH3:14])[CH3:13].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:28]2[CH2:27][CH2:26][N:25]([CH2:24][C:20]3[CH:19]=[C:18]([CH:23]=[CH:22][CH:21]=3)[C:17]([NH:16][C:12]([CH3:14])([CH3:15])[CH3:13])=[O:31])[CH2:30][CH2:29]2)=[O:8])=[CH:4][C:3]=1[CH3:11]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 755984-Amino-3-methylbenzoic acidHCID 111923Propylphosphonic anhydrideHCID 66877987N-tert-butyl-3-(piperazin-1-ylmethyl)benzamide

Product 1

HCID 57917707HCID 57917707, compoundYield 44.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution, of. 4-amino-3-methylbenzoic acid (3.31 mmol, 0.50 g), N-tert-butyl-3-(piperazin-1-ylmethyl)benzamide (3.45 mmol, 0.95 g) and triethylamine (14.35 mmol, 2.00 mL, 1.452 g) in dichloromethane (10 mL) was added 1-propanephosphonic acid cyclic anhydride (6.75 mmol, 4 mL, 4.30 g, 50% in ethyl acetate) dropwise. The mixture was allowed to stir for 1 hour. After this time ethyl acetate was added and the organic mixture was washed with saturated sodium hydrogen carbonate (×2), water (×2) and finally brine. The organic layer was dried with sodium sulfate and concentrated under vacuum to yield the title compound (0.60 g).

Workup

  1. washthe organic mixture was washed with saturated sodium hydrogen carbonate (×2), water (×2) and finally brine
  2. dry with materialThe organic layer was dried with sodium sulfate
  3. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-23301682e27b496fb980596df3913262
Source dataset
uspto-grants-2012_11
Patent number
US08314091B2

Reaction notes

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