Trifluoroacetic acid → HCID 136121545, compound

HRID 2062262Notes

Reaction equation

HRID 2062262 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:17]=[C:16]([N:18]2[CH2:23][CH2:22][CH2:21][C@@H:20]([NH:24]C(=O)OC(C)(C)C)[CH2:19]2)[C:15]2[C:10](=[CH:11][C:12]([CH3:32])=[CH:13][CH:14]=2)[N:9]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:24][C@@H:20]1[CH2:21][CH2:22][CH2:23][N:18]([C:16]2[C:15]3[C:10](=[CH:11][C:12]([CH3:32])=[CH:13][CH:14]=3)[N:9]=[C:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[OH:1])[N:17]=2)[CH2:19]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 136121491HCID 136121491, compound

Product 1

HCID 136121545HCID 136121545, compoundYield 85.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl(R)-1-(2-(2-hydroxyphenyl)-7-methylquinazolin-4-yl)piperidin-3-ylcarbamate (0.54 g, 1.24 mmol) was dissolved in CH2Cl2 (15 mL) followed by the addition of TFA (8 mL). The reaction was stirred for 1.5 h, and the solvents were evaporated to an oily liquid which was diluted with CH2Cl2 and neutralized with a 1 M aqueous NaOH solution. The organic layer was separated, and the aqueous layer was washed two times with CH2Cl2. After drying the combined organic phases over MgSO4, they were filtered, and concentrated to afford 2-(4-((R)-3-aminopiperidin-1-yl)-7-methylquinazolin-2-yl)phenol as a solid (0.354 g, 85%). LC/MS: m/z 335.7 (M+H)+ at 1.42 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA))

Workup

  1. customthe solvents were evaporated to an oily liquid which
  2. additionwas diluted with CH2Cl2
  3. customThe organic layer was separated
  4. washthe aqueous layer was washed two times with CH2Cl2
  5. dry with materialAfter drying the combined organic phases over MgSO4, they
  6. filtrationwere filtered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-e0d42384fc56436a81f83fc6129b3634
Source dataset
uspto-grants-2012_10
Patent number
US08283354B2

Reaction notes

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