Trifluoroacetic acid → HCID 178525873, compound

HRID 1819484Notes

Reaction equation

HRID 1819484 reaction equation
C([O:5][C:6](=[O:39])[CH2:7][NH:8][CH:9]1[CH2:14][CH2:13][CH:12]([CH2:15][NH:16][C:17]2[C:22]([N+:23]([O-:25])=[O:24])=[CH:21][N:20]=[C:19]([NH:26][CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[O:34][C:35]([F:38])([F:37])[F:36])[N:18]=2)[CH2:11][CH2:10]1)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[N+:23]([C:22]1[C:17]([NH:16][CH2:15][C@H:12]2[CH2:13][CH2:14][C@H:9]([NH:8][CH2:7][C:6]([OH:39])=[O:5])[CH2:10][CH2:11]2)=[N:18][C:19]([NH:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[O:34][C:35]([F:38])([F:37])[F:36])=[N:20][CH:21]=1)([O-:25])=[O:24]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69053878(4-{[5-Nitro-2-(2-trifluoromethoxy-benzylamino)-pyrimidin-4-ylamino]-methyl}-cyclohexylamino)-acetic acid tert-butyl ester

Product 1

HCID 178525873HCID 178525873, compoundYield 85.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (4-{[5-nitro-2-(2-trifluoromethoxy-benzylamino)-pyrimidin-4-ylamino]-methyl}-cyclohexylamino)-acetic acid tert-butyl ester (60 mg, 0.108 mmol) in DCM (1 mL) was added TFA (1 mL). The solution was allowed to stand at room temperature for 16 h before the solvent was removed in vacuo. The residue was taken up in water (1 mL) and 2 N NaOH added until the mixture reached pH 5. The mixture was diluted with water (3 mL) and filtered. The filtered solid was washed with water and Et2O before drying in vacuo to afford the target compound (46 mg, 85%) as a white solid, m/z 499 [M+1]+.

Workup

  1. customwas removed in vacuo
  2. addition2 N NaOH added until the mixture
  3. additionThe mixture was diluted with water (3 mL)
  4. filtrationfiltered
  5. washThe filtered solid was washed with water and Et2O
  6. custombefore drying in vacuo

Sources & evidence

ORD record
ord-b1ff595455974cd7915b40dbeaf12f9d
Source dataset
uspto-grants-2009_10
Patent number
US07601714B2

Reaction notes

Loading…