t-Butyl 2-[({2-(2,3-dihydro-1H-indol-1-yl)-4-[(4-fluorobenzyl)oxy]-5-pyrimidinyl}carbonyl)amino]acetate → 2-[({2-(2,3-dihydro-1H-indol-1-yl)-4-[(4-fluorobenzyl)oxy]-5-pyrimidinyl}carbonyl)amino]acetic acid

HRID 7436

Reaction equation

HRID 7436 reaction equation
[N:1]1([C:10]2[N:15]=[C:14]([O:16][CH2:17][C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=3)[C:13]([C:25]([NH:27][CH2:28][C:29]([O:31]C(C)(C)C)=[O:30])=[O:26])=[CH:12][N:11]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1>FC(F)(F)C(O)=O.ClCCl>[N:1]1([C:10]2[N:15]=[C:14]([O:16][CH2:17][C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=3)[C:13]([C:25]([NH:27][CH2:28][C:29]([OH:31])=[O:30])=[O:26])=[CH:12][N:11]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1

Participants

3

Reactant 1

HCID 9912947t-Butyl 2-[({2-(2,3-dihydro-1H-indol-1-yl)-4-[(4-fluorobenzyl)oxy]-5-pyrimidinyl}carbonyl)amino]acetate

Product 1

HCID 219905372-[({2-(2,3-dihydro-1H-indol-1-yl)-4-[(4-fluorobenzyl)oxy]-5-pyrimidinyl}carbonyl)amino]acetic acidYield 82.9%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

t-Butyl 2-[({2-(2,3-dihydro-1H-indol-1-yl)-4-[(4-fluorobenzyl)oxy]-5-pyrimidinyl}carbonyl)amino]acetate (210 mg, 0.4 mmol) was dissolved in trifluoroacetic acid-dichloromethane (4:1, 2 mL) and the mixture was stirred at room temperature for 15 min. The reaction mixture was concentrated under reduced pressure and the precipitated crystals were recrystallized from ethyl acetate to give the title compound (140 mg, 70%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe precipitated crystals were recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-f6f742a697e84fcea25f99e5bc06f882
Source dataset
uspto-grants-2006_08
Patent number
US07087597B1

Linked notes

Loading…