Trifluoroacetic acid → HCID 18697949, compound

HRID 2289485Notes

Reaction equation

HRID 2289485 reaction equation
C([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:25]=[CH:24][N:23]=[C:22]([Cl:26])[N:21]=3)=[CH:16][N:15]=2)[CH2:10][CH2:9]1)=[O:7])(C)(C)C.FC(F)(F)C(O)=O.ClC(O[CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)=O>ClCCl>[CH2:38]([O:5][C:6]([N:8]1[CH2:9][CH2:10][N:11]([C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:25]=[CH:24][N:23]=[C:22]([Cl:26])[N:21]=3)=[CH:16][N:15]=2)[CH2:12][CH2:13]1)=[O:7])[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 10387Benzyl chloroformateHCID 18545618HCID 18545618, compound

Product 1

HCID 18697949HCID 18697949, compoundYield 89.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 4-(2-(4-tert-butoxycarbonylpiperazin-1-yl)pyrid-5-yl)-2-chloropyrimidine (8.00 g, 21.30 mmol) in dichloromethane (60 ml) was treated with trifluoroacetic acid and the resulting mixture stirred at room temperature for 2 h, then evaporated and reconcentrated four times from dichloromethane. The residue was suspended in a mixture of dichloromethane (150 ml) and saturated aqueous sodium bicarbonate (150 ml) then treated portionwise with benzyl chloroformate (4.00 g, 23.44 mmol) in dichloromethane (5 ml). The resulting mixture was stirred rapidly for 18 h then the organic phase was separated, dried (MgSO4) and evaporated to give the crude product which was purified by recrystallisation (ethyl acetate-hexane) to afford the title compound (7.85 g) as an off-white solid m.p. 145-147°. δH (CDCl3) 3.65-3.77 (8H, m), 5.18 (2H, s), 6.73 (1H, d, J 9.1 Hz), 7.36 (5H, m), 7.52 (1H, d, J 5.4 Hz), 8.31 (1H, dd, J 2.3, 8.1 Hz), 8.54 (1H, d, J 5.4 Hz) and 8.86 (1H, d, J 2.3 Hz).

Workup

  1. customevaporated
  2. additionThe residue was suspended in a mixture of dichloromethane (150 ml) and saturated aqueous sodium bicarbonate (150 ml)
  3. stirringThe resulting mixture was stirred rapidly for 18 h
  4. customthe organic phase was separated
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customto give the crude product which
  8. customwas purified by recrystallisation (ethyl acetate-hexane)

Sources & evidence

ORD record
ord-dc1d461df9694330b75eff3809baf896
Source dataset
uspto-grants-2000_07
Patent number
US06093716

Reaction notes

Loading…