Trifluoroacetic acid → HCID 89922533, compound

HRID 921905Notes

Reaction equation

HRID 921905 reaction equation
C(O)(C(F)(F)F)=O.C(OC([NH:15][C:16]1[C:17]([Cl:37])=[C:18]([CH:24]2[O:29][CH2:28][CH2:27][N:26](C(OC(C)(C)C)=O)[CH2:25]2)[CH:19]=[C:20]([C:22]#[N:23])[CH:21]=1)=O)(C)(C)C>C(Cl)Cl>[NH2:15][C:16]1[CH:21]=[C:20]([CH:19]=[C:18]([CH:24]2[O:29][CH2:28][CH2:27][NH:26][CH2:25]2)[C:17]=1[Cl:37])[C:22]#[N:23]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 89922662HCID 89922662, compound

Product 1

HCID 89922533HCID 89922533, compoundYield 96.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (4.5 mL) was added to a solution of tert-butyl 2-(3-((tert-butoxycarbonyl)amino)-2-chloro-5-cyanophenyl)morpholine-4-carboxylate (252 mg, 0.575 mmol) in DCM (4.5 mL) at room temperature. After 0.5 hr, the solvent was removed. The residue in was dissolved in MeOH and this was applied onto an SCX column. After washing with MeOH, the product was eluted with 2N NH3 in MeOH to give 3-amino-4-chloro-5-(morpholin-2-yl)benzonitrile (132 mg) as an oil. This was dissolved in DCM (7 mL) and TEA (0.096 mL, 0.69 mmol) and BOC2O (0.16 mL, 0.69 mmol) were added. After stirring overnight, the solvent was removed and radial silica gel chromatography eluting with hexane containing 0 to 30% EtOAc afforded tert-butyl 2-(3-amino-2-chloro-5-cyanophenyl)morpholine-4-carboxylate (203 mg).

Workup

  1. customthe solvent was removed
  2. dissolutionThe residue in was dissolved in MeOH
  3. washAfter washing with MeOH
  4. washthe product was eluted with 2N NH3 in MeOH

Sources & evidence

ORD record
ord-8dece6d25a8e4e22a7e95bbc60788b0e
Source dataset
uspto-grants-2016_03
Patent number
US09273057B2

Reaction notes

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