Dichloromethane → 2-(3,5-Bis-(4-fluoro-phenyl)-(1,2,4)triazol-1-yl)-1-(4-(5-methoxy-pyrimidin-2-yl)-piperazin-1-yl)-ethanone

HRID 336383Notes

Reaction equation

HRID 336383 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]=[C:11]([C:13]3[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=3)[N:10]([CH2:20][C:21](O)=[O:22])[N:9]=2)=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.Cl.[CH3:34][O:35][C:36]1[CH:37]=[N:38][C:39]([N:42]2[CH2:47][CH2:46][NH:45][CH2:44][CH2:43]2)=[N:40][CH:41]=1.C(Cl)Cl>CN(C=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]=[C:11]([C:13]3[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=3)[N:10]([CH2:20][C:21]([N:45]3[CH2:46][CH2:47][N:42]([C:39]4[N:38]=[CH:37][C:36]([O:35][CH3:34])=[CH:41][N:40]=4)[CH2:43][CH2:44]3)=[O:22])[N:9]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 81531Diisopropylethylamine2×HCID 86686517(3,5-bis-(4-Fluoro-phenyl)-(1,2,4)triazol-1-yl)-acetic acidHCID 866866095-Methoxy-2-piperazin-1-yl-pyrimidine hydrochloride

Product 1

HCID 716665642-(3,5-Bis-(4-fluoro-phenyl)-(1,2,4)triazol-1-yl)-1-(4-(5-methoxy-pyrimidin-2-yl)-piperazin-1-yl)-ethanoneYield 20.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

100 mg (3,5-bis-(4-fluoro-phenyl)-(1,2,4)triazol-1-yl)-acetic acid was dissolved in 2 mL DMF. 163 mg PFTU and 0.5 mL DIPEA were added to this solution and the mixture was stirred for 7 min at RT. Then, 88 mg 5-Methoxy-2-piperazin-1-yl-pyrimidine hydrochloride and 0.11 mL DIPEA dissolved in 1.5 mL DMF were added and the reaction was stirred 3 h at RT. Then, a saturated sodiumhydrogencarbonate solution and CH2Cl2 were added, the organic phase was separated and the solvent was removed. The residue was purified by HPLC and crystallized with diethylether to give 32 mg of the desired compound. Rt: 0.82 min (method E), (M+H)+: 492

Workup

  1. additionwere added
  2. stirringthe reaction was stirred 3 h at RT
  3. customthe organic phase was separated
  4. customthe solvent was removed
  5. customThe residue was purified by HPLC
  6. customcrystallized with diethylether

Sources & evidence

ORD record
ord-17e437f69b6c4c68b4d9eb90bdbaf8d1
Source dataset
uspto-grants-2014_11
Patent number
US08889677B2

Reaction notes

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