Triethylamine → HCID 57917695, compound

HRID 1878336Notes

Reaction equation

HRID 1878336 reaction equation
[NH2:1][C:2]1[C:10]([F:11])=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][C:3]=1[F: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[C:3]([F:12])=[CH:4][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])=[CH:9][C:10]=1[F:11]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 111923Propylphosphonic anhydrideHCID 2821334-amino-3,5-difluorobenzoic acidHCID 66877987N-tert-butyl-3-(piperazin-1-ylmethyl)benzamide

Product 1

HCID 57917695HCID 57917695, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 4-ammo-3,5-difluorobenzoic acid (1 g, 5.78 mmoles), N-tert-butyl-3-(piperazin-1-ylmethyl)benzamide (1.59 g, 5.78 mmoles) and triethylamine (4 mL) in dichloromethane (30 mL) was added 1-propanephosphonic acid cyclic anhydride (8 mL, 50% solution in ethyl acetate). After 2 hours stirring, the reaction mixture was diluted with ethyl acetate and washed with sodium carbonate (aqueous) (3×), dried (magnesium sulfate) and concentrated under reduced pressure to give the title compound (2.24 g) as an off-white foam.

Workup

  1. washwashed with sodium carbonate (aqueous) (3×)
  2. dry with materialdried (magnesium sulfate)
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5bbc9fc86f4c4c3ea7d4d0b906b2f5a2
Source dataset
uspto-grants-2012_11
Patent number
US08314091B2

Reaction notes

Loading…