HCID 86757564, compound → HCID 69360635, compound

HRID 395855Notes

Reaction equation

HRID 395855 reaction equation
[Cl:1][C:2]1[CH:42]=[CH:41][C:5]([C:6]([NH:8][C:9]2[C:10]([NH:24][C:25]([O:27][CH:28]([CH:35]3[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]3)[C:29]3[CH:34]=[CH:33][N:32]=[CH:31][CH:30]=3)=[O:26])=[CH:11][C:12]([NH:15]NC(OC(C)(C)C)=O)=[CH:13][CH:14]=2)=[O:7])=[CH:4][CH:3]=1>FC(F)(F)C(O)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([NH:8][C:9]2[C:10]([NH:24][C:25]([O:27][CH:28]([CH:35]3[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]3)[C:29]3[CH:30]=[CH:31][N:32]=[CH:33][CH:34]=3)=[O:26])=[CH:11][C:12]([NH2:15])=[CH:13][CH:14]=2)=[O:7])=[CH:41][CH:42]=1

Participants

3

Reactant 1

HCID 86757564HCID 86757564, compound

Product 1

HCID 69360635HCID 69360635, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

N1-(4-Chlorobenzoyl)-N2-[1-(4-pyridyl)piperidin-4-ylmethoxycarbonyl]-N4-tert-butoxycarbonylamino-1,2,4-benzenetriamine (150 mg, 0.26 mmol) was dissolved in trifluoroacetic acid (2 mL). After 2 h, the mixture was concentrated and the residue partitioned between EtOAc and 1N NaOH and sat'd NaHCO3 (aq). The aqueous layer was washed with EtOAc (2×) and the combined extracts were dried (MgSO4) and concentrated. The residue was purified by chromatography (9:1 CH2Cl2:MeOH) affording 110 mg (89%) of the title compound.

Workup

  1. concentrationthe mixture was concentrated
  2. customthe residue partitioned between EtOAc and 1N NaOH and sat'd NaHCO3 (aq)
  3. washThe aqueous layer was washed with EtOAc (2×)
  4. dry with materialthe combined extracts were dried (MgSO4)
  5. concentrationconcentrated
  6. customThe residue was purified by chromatography (9:1 CH2Cl2:MeOH)

Sources & evidence

ORD record
ord-5b9212584d5245ad93fe70767d135515
Source dataset
uspto-grants-2003_08
Patent number
US06605626B2

Reaction notes

Loading…