Diethyl Ether → HCID 58933821, compound

HRID 854299Notes

Reaction equation

HRID 854299 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([CH2:17][NH:18][C:19]([C:21]2[CH:26]=[CH:25][N:24]=[C:23]([NH:27]CC3C=CC(OC)=CC=3OC)[CH:22]=2)=[O:20])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O.CCOCC>ClCCl>[CH2:1]([O:8][C:9]([N:11]1[CH2:12][CH2:13][CH:14]([CH2:17][NH:18][C:19]([C:21]2[CH:26]=[CH:25][N:24]=[C:23]([NH2:27])[CH:22]=2)=[O:20])[CH2:15][CH2:16]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 6422Trifluoroacetic acidHCID 10301538HCID 10301538, compound

Product 1

HCID 58933821HCID 58933821, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-({[2-(2,4-Dimethoxy-benzylamino)-pyridine-4-carbonyl]-amino}-methyl)-piperidine-1-carboxylic acid benzyl ester (EXAMPLE 171) (124 mg) in dichloromethane (5 mL) was treated with trifluoroacetic acid (0.5 mL). After 30 min, the reaction mixture was partitioned between EtOAc and dilute sodium bicarbonate solution. The organic layer was washed with brine, dried and the solvent evaporated to give the crude product which was stirred with ether (3mL) and filtered to give the 4-{[(2-amino-pyridine-4-carbonyl)-amino]-methyl}-piperidine-1-carboxylic acid benzyl ester as a white solid.

Workup

  1. customthe reaction mixture was partitioned between EtOAc and dilute sodium bicarbonate solution
  2. washThe organic layer was washed with brine
  3. customdried
  4. customthe solvent evaporated
  5. customto give the crude product which
  6. filtrationfiltered

Sources & evidence

ORD record
ord-08a1b7f8d0174a2782cec7cc599877e5
Source dataset
uspto-grants-2007_08
Patent number
US07259157B2

Reaction notes

Loading…