Trifluoroacetic acid → N4-[4-tert-butyl-2-(piperidin-4-yloxy)benzoyl]-N3-(4-methoxybenzoyl)-3,4-pyridinediamine

HRID 1445437Notes

Reaction equation

HRID 1445437 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:40]=[C:39]([C:41]([CH3:44])([CH3:43])[CH3:42])[CH:38]=[CH:37][C:16]=2[C:17]([NH:19][C:20]2[CH:25]=[CH:24][N:23]=[CH:22][C:21]=2[NH:26][C:27](=[O:36])[C:28]2[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=2)=[O:18])[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl.CO>[C:41]([C:39]1[CH:38]=[CH:37][C:16]([C:17]([NH:19][C:20]2[CH:25]=[CH:24][N:23]=[CH:22][C:21]=2[NH:26][C:27](=[O:36])[C:28]2[CH:29]=[CH:30][C:31]([O:34][CH3:35])=[CH:32][CH:33]=2)=[O:18])=[C:15]([O:14][CH:11]2[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]2)[CH:40]=1)([CH3:44])([CH3:42])[CH3:43]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69492771N4-[2-(1-tert-Butoxycarbonylpiperidin-4-yloxy)-4-tert-butylbenzoyl]-N3-(4-methoxybenzoyl)-3,4-pyridinediamine

Product 1

HCID 11576987N4-[4-tert-butyl-2-(piperidin-4-yloxy)benzoyl]-N3-(4-methoxybenzoyl)-3,4-pyridinediamineYield 104.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To an ice-water bath-chilled solution of N4-[2-(1-tert-butoxycarbonylpiperidin-4-yloxy)-4-tert-butylbenzoyl]-N3-(4-methoxybenzoyl)-3,4-pyridinediamine (460 mg, 764 micromoles) in dichloromethane (15 mL) was added trifluoroacetic acid (5 mL) and the mixture stirred on ice for 90 min. The mixture was then concentrated in vacuo, the oily residue redissolved in 1:1 dichloromethane:toluene (10 mL) and re-concentrated in vacuo to provide a pale tan-yellow oil. The oil was dissolved in methanol (10 mL) and applied to a 10 gram×60 cubic centimeter strong cation exchange solid phase extraction column (SCX, Varian Sample Preparation Products, Harbor City, Calif.) that had been conditioned with methanol. After sample application, the cartridge was washed with methanol (4×50 mL) and the product was eluted with 3:1 chloroform:(2 M NH3 in methanol) (3×40 mL). The eluates were concentrated in vacuo to afford N4-[4-tert-butyl-2-(piperidin-4-yloxy)benzoyl]-N3-(4-methoxybenzoyl)-3,4-pyridinediamine as a yellow oil (400 mg, 104%). This material was used without further purification.

Workup

  1. concentrationThe mixture was then concentrated in vacuo
  2. dissolutionthe oily residue redissolved in 1:1 dichloromethane
  3. concentrationtoluene (10 mL) and re-concentrated in vacuo
  4. customto provide a pale tan-yellow oil
  5. extractionapplied to a 10 gram×60 cubic centimeter strong cation exchange solid phase extraction column (SCX, Varian Sample Preparation Products, Harbor City, Calif.) that
  6. washAfter sample application, the cartridge was washed with methanol (4×50 mL)
  7. washthe product was eluted with 3:1 chloroform
  8. concentrationThe eluates were concentrated in vacuo

Sources & evidence

ORD record
ord-0fd053a456274050a83b3ccbb0529e40
Source dataset
uspto-grants-2010_02
Patent number
US07666866B2

Reaction notes

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