Dimethylformamide → N1-(4-Difluoromethoxybenzoyl)-N2-[1-(4-pyridyl)piperidin-4-ylmethoxycarbonyl]-1,2-benzenediamine Hydrochloride

HRID 427669

Reaction equation

HRID 427669 reaction equation
N1C=CC([N:7]2[CH2:12][CH2:11][CH:10]([CH2:13][O:14][C:15]([NH:17][C:18]3[C:19]([NH2:24])=[CH:20][CH:21]=[CH:22][CH:23]=3)=[O:16])[CH2:9][CH2:8]2)=CC=1.[F:25][CH:26]([F:37])[O:27][C:28]1[CH:36]=[CH:35][C:31]([C:32]([OH:34])=O)=[CH:30][CH:29]=1.[ClH:38].CN(C)[CH2:41][CH2:42][CH2:43][N:44]=[C:45]=NCC.[CH3:50]N(C=O)C>>[ClH:38].[F:37][CH:26]([F:25])[O:27][C:28]1[CH:29]=[CH:30][C:31]([C:32]([NH:24][C:19]2[C:18]([NH:17][C:15]([O:14][CH:13]([CH:10]3[CH2:9][CH2:8][NH:7][CH2:12][CH2:11]3)[C:41]3[CH:42]=[CH:43][N:44]=[CH:45][CH:50]=3)=[O:16])=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:34])=[CH:35][CH:36]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 7373604-(Difluoromethoxy)benzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 10829995N2-[1-(4-pyridyl)piperidin-4-yl]methoxycarbonyl-1,2-benzenediamine

Product 1

HCID 86757561N1-(4-Difluoromethoxybenzoyl)-N2-[1-(4-pyridyl)piperidin-4-ylmethoxycarbonyl]-1,2-benzenediamine HydrochlorideYield 38%

Procedure

To a solution of N1-[1-(4-pyridyl)piperidin-4-yl-methoxycarbonyl]-1,2-benzenediamine (0.2 g, 0.6 mmol) and 4-difluoromethoxybenzoic acid (0.23 g, 1.2 mmol) in DMF (10 mL) was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.24 g, 1.2 mmol). After stirring overnight, the solvent was removed in vacuo and the residue was partitioned between ethyl acetate (300 mL) and 1 N NaOH (150 ml). The layers were separated and the organic phase was washed with brine, dried with MgSO4, filtered and concentrated in vacuo. The residue was purified by RPHPLC method A and the fractions containing pure product were combined and lypholized to give 123 mg (38%) of the title product as a white solid.

Workup

  1. customthe solvent was removed in vacuo
  2. customthe residue was partitioned between ethyl acetate (300 mL) and 1 N NaOH (150 ml)
  3. customThe layers were separated
  4. washthe organic phase was washed with brine
  5. dry with materialdried with MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by RPHPLC method A
  9. additionthe fractions containing pure product

Sources & evidence

ORD record
ord-ede4f5886f7c4bdca988094cfef1c0e2
Source dataset
uspto-grants-2001_11
Patent number
US06313122B1

Linked notes

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