Trifluoroacetic acid → HCID 178511539, compound

HRID 1819465Notes

Reaction equation

HRID 1819465 reaction equation
C(OC(=O)[NH:7][CH:8]1[CH2:13][CH2:12][CH:11]([CH2:14][NH:15][C:16]2[C:21]([Br:22])=[CH:20][N:19]=[C:18]([NH:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[O:31][C:32]([F:35])([F:34])[F:33])[N:17]=2)[CH2:10][CH2:9]1)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:7][C@H:8]1[CH2:9][CH2:10][C@H:11]([CH2:14][NH:15][C:16]2[C:21]([Br:22])=[CH:20][N:19]=[C:18]([NH:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[O:31][C:32]([F:33])([F:34])[F:35])[N:17]=2)[CH2:12][CH2:13]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57885517HCID 57885517, compound

Product 1

HCID 178511539HCID 178511539, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

(4-{[5-Bromo-2-(2-trifluoromethoxy-benzylamino)-pyrimidin-4-ylamino]-methyl}-cyclohexyl)-carbamic acid tert-butyl ester (75 mg, 0.13 mmol) was dissolved in CH2Cl2 (2 mL). To this solution was added TFA (2 mL) and the reaction was stirred at 25° C. for 1 h. The volatiles were removed in vacuo. The crude was redissolved in CH2Cl2 and poured into 10% aqueous NaHCO3. The aqueous phase was separated and extracted two more times with CH2Cl2. The organic layers were combined, dried (Na2SO4), decanted and concentrated. The crude was purified via flash chromatography (SiO2, 2-10% (NH4OH:CH3OH:CH2Cl2—CH2Cl2)) to afford 45 mg (73%) of the target compound, m/z 474.38 [M+1]+.

Workup

  1. customThe volatiles were removed in vacuo
  2. dissolutionThe crude was redissolved in CH2Cl2
  3. additionpoured into 10% aqueous NaHCO3
  4. customThe aqueous phase was separated
  5. extractionextracted two more times with CH2Cl2
  6. dry with materialdried (Na2SO4)
  7. customdecanted
  8. concentrationconcentrated
  9. customThe crude was purified via flash chromatography (SiO2, 2-10% (NH4OH:CH3OH:CH2Cl2—CH2Cl2))

Sources & evidence

ORD record
ord-292b9269e7c247b184c97a78f87a1827
Source dataset
uspto-grants-2009_10
Patent number
US07601714B2

Reaction notes

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