Trifluoroacetic acid → HCID 67285084, compound

HRID 2093778Notes

Reaction equation

HRID 2093778 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][NH:5][C:6]([C:8]1[CH:13]=[CH:12][C:11]([NH:14][C:15]2[N:20]=[C:19]([O:21][CH2:22][C:23]([F:26])([F:25])[F:24])[N:18]=[C:17]([NH:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][NH:36]C(=O)OC(C)(C)C)[N:16]=2)=[CH:10][CH:9]=1)=[O:7].C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][NH:27][C:17]1[N:18]=[C:19]([O:21][CH2:22][C:23]([F:25])([F:26])[F:24])[N:20]=[C:15]([NH:14][C:11]2[CH:12]=[CH:13][C:8]([C:6]([NH:5][CH2:4][CH2:3][CH2:2][Cl:1])=[O:7])=[CH:9][CH:10]=2)[N:16]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67284875HCID 67284875, compound

Product 1

HCID 67285084HCID 67285084, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-butyl (8-((4-((4-((3-chloropropyl)carbamoyl)phenyl)amino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-yl)amino)octyl)carbamate (264 mg, 0.418 mmol) was dissolved in a 1:1 TFA (1 ml, 12.98 mmol)/DCM (1 mL). The reaction was stirred for 1 h. The solvent was removed under vacuum and the residue was dissolved in EtOAc and washed with saturated sodium bicarbonate solution, then brine. The organic layer was collected and dried over sodium sulfate, and concentrated under vacuum to give 222 mg (100%) 4-(4-(8-aminooctylamino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-ylamino)-N-(3-chloropropyl)benzamide as a white solid.

Workup

  1. customThe solvent was removed under vacuum
  2. dissolutionthe residue was dissolved in EtOAc
  3. washwashed with saturated sodium bicarbonate solution
  4. customThe organic layer was collected
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-2fa078e7be6f4a99a98b837295d1aa3e
Source dataset
uspto-grants-2013_05
Patent number
US08445490B2

Reaction notes

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